jeffrey t. kushner chem 508 protein/carbohydrate ...kushnert/508/kushner_thesis_lessonplan.pdfthe...

Jeffrey T. Kushner Chem 508 Lesson Plan Protein/Carbohydrate Properties Summary The lessons found in this appendix fall within the standard chapters of Organic Compounds, and BioChemicals, or integrated chapters of Food Chemistry, for a high school 10th grade chemistry class. These chapters are commonly covered at the end of the year but, depending on the scope and sequence of the teacher, may be covered at other times of the year. These lessons have been constructed for college prep or honors level classes, but can be integrated to higher or lower levels. Adaptive techniques could be to increase overall lesson duration, append difficult vocabulary, provide extra prompts and support with PIM’s, and/or modify structured practice and independent practice questions. These lessons use a variety of instructional techniques to maximize different student learning styles that are found in a diverse classroom. At the beginning of the lesson, students are introduced to proteins through a section of notes. A PIM will allow students to build upon previously learned knowledge, acids and bases, by examining acid/base properties of amino acids. During the examination of these properties, students will perform an inquiry lab discovering the acid/base properties of the protein Casein. After completion of the lab, the class will develop and review the community knowledge gathered throughout the PIM. Students transition from the first section, proteins, to the second section, carbohydrates, by comparing the functional differences of these two chemical groups for the human body. Lessons 4-5 then introduce and examine carbohydrates, the second of three organic compounds that could be covered (the final being lipids, not included in this lesson packet). After an introductory section of notes, students will then perform tests on known and unknown samples of carbohydrates. This inquiry approach will allow students to discover the types of carbohydrates found in certain foods. The final lesson in this section examines a recent court case where the makers of Equal sued the makers of Splenda® for an advertising slogan. This lesson provides an opportunity for students to examine production techniques for an artificial sweetener and discuss ramifications of false advertising. PA State Standards Covered in Lessons 3.2.10(12)A—Apply/evaluate knowledge and understanding about the nature of

scientific knowledge 3.2.10(12)B—Apply/evaluate knowledge and organize scientific phenomena in varied

ways 3.2.10(12)C—Apply the elements of scientific inquiry to problem solve(one or multi-step) 3.4.10(12)A—explain/apply concepts about the structure of matter

2 Kushner-Lesson Plan

Class Session 1 Overview (Setting) This lesson is designed for a college prep chemistry class with an extended lab period. (This lab period may coincide with the lecture period or it may follow at some other time.) Students are connecting knowledge learned in last years Biology course and now beginning to develop a more comprehensive and complete understanding of the chemical nature of proteins. They will find by the end of these lessons that proteins are complex, essential molecules necessary for life. Objective

• Students will be able to describe proteins at the symbolic level of representation. • Students will be able to describe proteins at the macroscopic level of

representation. • Students will be able to describe proteins at the microscopic level of

representation. • Students will be able to examine the structure of an amino acid sequence. • Students will be able to predict the acidic or basic properties of an amino acid.

Pre-Class Activity KWL Chart

K—What did students already know about proteins and acid/base properties?

W—What did students want to know about proteins and acid/base properties? L—What did students learned about proteins and acid/base properties after lesson.


Content—Protein Notes (Introduction) Proteins

Organic Compound made of the elements � Carbon � Hydrogen � Oxygen

� Nitrogen � Sulfur

Protein background Amino Acids

20 building blocks Molecules that combine to make a protein Two or more amino acids form a protein

Functions in Humans � Structure of an

organism � Hair � Nails � Contracting Muscle

� Immunity � Speeding up

chemical reactions • enzymes

Structure Primary 1º

Amino acid order bonded covalently

Secondary 2º

Folding of backbone α -helices β-pleated sheets

Tertiary 3º 3-D folding of 2º

Quaternary 4º Orientation of subunits of 3º units


Structured Practice (Class work) I) PIM

A) Acid-Base Properties of Amino Acids 1) Initial Question

(a) How are proteins (and the amino acids that make up proteins) affected by pH?

2) Existing Information 3) Reflect and Organize 4) Results & Peer Review 5) New Information 6) Community Knowledge

Independent Practice (Homework)

� Pre-Lab Activity o Read lab—“ o Copy procedure & data table in notebook o Answer Pre-lab questions

Closure KWL Chart -students will individually complete the ‘L’ column -identifying concepts learned through lesson


Class Sessions 2-3 Overview

This lesson is designed for a college prep chemistry class with an extended lab period. (This lab period may coincide with the lecture period or it may follow at some other time.) Students are connecting knowledge learned in last years Biology course and now beginning to develop a more comprehensive and complete understanding of the chemical nature of proteins. Students are continuing the PIM investigation on the acid/base properties of proteins. This class session is best carried out in a laboratory setting during an extended lab period or over two concurrent class periods.

Objectives

• Students will be able to precipitate the protein Casein from milk using 3M HCl • Students will be able to re-dissolve the protein Casein into milk using 3M NaOH • Students will be able to examine the structure of an amino acid sequence. • Students will be able to predict the acidic or basic properties of an amino acid.

Pre-Class Activity Students will review information gathered yesterday in small groups. They will discuss the information recorded in the KWL chart. After a five minute period, they will then report to class the (L) Learned knowledge from yesterday’s class.

Structured Practice (Class work) I) PIM

A) Acid-Base Properties of Amino Acids 1) Initial Question

(a) How are proteins (and the amino acids that make up proteins) affected by pH?

2) Existing Information 3) Reflect and Organize 4) Results & Peer Review 5) New Information

(a) A stuffy of the Milk Protein: Casein 6) Community Knowledge

II) Assessment A) Student groups will be monitored through progression of PIM. Prompts and new

information will be provided as requested by groups. B) Development of community knowledge and lab result comparison will be used to

assess classes level of understanding. Students will continue with the PIM activity by completing the Casein Lab activity to gain insight on how protein solutions are affected by pH.


Lab Activity How is a protein solution affect by pH? A study of the Milk Protein: Casein. Independent Practice

� Lab Reflection Essay Students will write a four-paragraph essay reflecting on the lab procedure, lab observations, knowledge of the lab, and ways the lab experience could have been improved. Use the outline below as a guide for 4 paragraphs.


Class Session 4-5 Overview

This lesson is designed for a college prep chemistry class with an extended lab period. (This lab period may coincide with the lecture period or it may follow at some other time.) Students are connecting knowledge learned in last years Biology course and now beginning to develop a more comprehensive and complete understanding of the chemical nature of proteins. Students are Students are beginning the class of organic compounds: carbohydrates.

Objective

• Students will be able to describe the roles of carbohydrates in the human body. • Students will be able to describe carbohydrates at the symbolic level of

representation. • Students will be able to describe carbohydrates at the macroscopic level of

representation. • Students will be able to describe carbohydrates at the microscopic level of

representation. • Students will be able to compare and contrast the different groups of

carbohydrates.

Pre-Class Activity Students will work in pairs and will be given 5 minutes to complete a food—chemical table. They will be asked to list foods that contain proteins or carbohydrates. They will then be asked to apply one three labels: short-term energy, long-term energy, or repair/rebuild tissue. At the end of 5 minutes, students will be given five minutes to report their findings to the class.

Content—Direct Instruction (Carbohydrate Notes) I. Carbohydrates A. Organic Compound 1. Contains atoms of a. Carbon b. Hydrogen

c. Oxygen d. ration 1:2:1

B. Used in humans 1. to store short term energy for cells

2. to store sugar (moderate term) energy in liver for cells C. Groups of Carbohydrates 1. Based on number of repeating units a. Monosaccharide—simple (single) sugar -‘mono’ = 1 -‘saccharide’ = sugar -glucose

b. Disaccharide—double sugar -‘di’ = 2 -‘saccharide’ = sugar -sucrose (table sugar)

c. Polysaccharide -‘poly’ = many -‘saccharide’ = sugar- -starch

D. Representation methods of Carbohydrates 1. Fischer projections 2. Hawthorn projections 3. Neumann projections


Laboratory Activity Testing for Carbohydrates (known and unknown tests)

Using Benedicts solution and iodine, students will be given known carbohydrate groups to determine how monosaccharides, disaccharides, and polysaccharides (starches) can be tested. Once lab groups have produced a testing carbohydrate table, they will test a variety of substances (honey(aq), apple juice, oats(aq), table sugar(aq), and confectioners sugar(aq), to determine which type of carbohydrate is present.

Independent Practice Carbohydrate sweeteners vs. low calorie sweeteners vs. no calorie sweeteners Students will be asked to pick one of three categories from above and research various perspectives using the computer. They are asked to present a one page essay defending their sweetener type vs. the other two types. In the essay, students will identify the beneficial reasons their sweetener should be consumed and why the other sweeteners should be avoided. Students will be given three days to complete the assignment. Upon arriving in class on the forth day, they will be asked to form three groups where the sweetener types will be homogenously organized. They will be given ten minutes to discuss their findings. After ten minutes. one student from each sweetener type will form a new group so each sweetener type is represented. They will be asked to present their findings and defend their sweetener to their new group of peers.


Class Session 6 Overview

This lesson is designed for a college prep chemistry class with an extended lab period. (This lab period may coincide with the lecture period or it may follow at some other time.) Students are connecting knowledge learned in last years Biology course and now beginning to develop a more comprehensive and complete understanding of the chemical nature of proteins. Students are Students are continuing with the study of carbohydrates by examining sugar substitutes. Specifically, they will compare two sugar substitutes and evaluate a recent lawsuit between the makers of sucralose and the makers of aspartame.

Objective

• Students will evaluate a current event (lawsuit) between two chemical companies.

• Students will analyze a chemical synthesis for sucralose to determine how it is made.

• Students will evaluate advertisement schemes to determine if a product is advertised appropriately.

• Students will develop

Pre-Class Activity Students will be given single serving packs of table sugar, cane sugar, Sweet’N low, Equal and Splenda® to determine if there is a taste difference between them. Students will then be given the structures of sucrose, aspartame, saccharin, and sucralose to determine if there are any structural similarities or differences between the molecules.

Structured Practice (Classwork) II) PIM

A) Artificial Sweetener Advertising 1) Initial Question

(a) Can the makers of Splenda® use the advertising slogan “Tastes like sugar because it is made from sugar?”

2) Existing Information 3) Reflect and Organize 4) Results & Peer Review 5) New Information 6) Community Knowledge

III) Assessment A) Student groups will be monitored through progression of PIM. Prompts and new

information will be provided as requested by groups. B) Development of community knowledge and comparison to trial verdict will be

used to determine classes understanding.


Independent Practice You are the chief advertising officer of a new company called ProMetron. One of your new accounts deals with a chemical called Neoculin. Neoculin is a sweet-tasting protein that is going to be used as a low (no) calorie sweetener. Since it is 37,500 times sweeter than sucrose (table sugar), only a small amount is needed to provide a food or beverage with a sweet taste. Since the amount is so small, someone consuming a food or beverage made from Neoculin sustains no caloric intake. Develop an advertising slogan and advertising storyboard for the company and/or the new low calorie sweetener. (This campaign can be through any media type.)


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Initial Question How are proteins (and the amino

acids that make up proteins)

affected by pH?

Existing Information Acids/Bases Organic Molecules -proton donor/acceptor -Proteins -pH Amino Acids Peptide Bonds

Reflect And Organize (Lab) How is a protein solution affected by pH?

Data Collection Students will use a basic solution of the milk protein (casein) and titrate it with 3M HCl. Upon completion of titration, they will re-dissolve protein with 3M NaOH.

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New Information Needed? -Casein precipitates at a pH of around 6. (eI point). -Amino Acid sequence of Casein will be provided.

Students will identify charged R-groups of amino acids in each protein.

Results Solution turns cloudy as pH drops. Casein precipitates at about pH of 6. Continued addition of HCl causes the protein to re-dissolve. Titration with 3M NaOH returns protein and solution to original pH and dissolved states.

Community Knowledge Side chains of some amino acids contain acidic or basic groups. The isoelectric point of the protein determines that the protein is uncharged and displays minimum water solubility. At a high pH the protein carries a negative charge. At a low pH the protein carries a positive charge. Ionic forms of the protein are water soluble.

Peer Review Students will collaborate data and determine that the change in state is due to the R-groups on the Amino Acid sequence.

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Lab: Casein and pH Overview Proteins are polymers of amino acids. The amine group and carboxylic acid group bonded to the same carbon on one amino acid form peptide bonds with two neighboring amino acids to build the polymer chain. When this happens, these groups are no longer available to accept or donate protons. Acidic or basic amino acid side groups remain free to accept or donate protons. Safety

Eye goggles and lab apron are required for this lab. 3M HCl and 3M NaOH are caustic. They can cause skin irritation and burns. Wash area immediately with water and contact the teacher if your skin comes in contact with either. Glass buret.

Pre Lab Questions

1. Describe the potential structural organization patterns that may exist for the protein ‘Casein’.

2. Hypothesize what would happen if 3M HCl or 3M NaOH were added to egg whites (which contain the protein egg white lysozome).

3. What would cause your hypothesis to occur? 4. Hypothesize what will happen to casein that is in an aqueous solution when

3M HCl is added. 5. Hypothesize what will happen to casein that is in an aqueous solution when

3M NaOH is added.

Procedure 1. Place 250mL of a basic 0.25% aqueous solution of casein (a protein found in

milk) in a 400 mL beaker. 2. Stir solution at medium speed with magnetic stirrer and magnetic stir bar. 3. Use a pH electrode and pH meter to monitor and read pH. 4. Using a burret, add 3M HCl solution several drops at a time.

a. After each addition, record amount of HCl added, pH, and observations of solution.

5. Continue until pH of solution reaches 2 6. Transfer beaker to burret of 3M NaOH. 7. Add 3M NaOH several drops at a time.

a. After each addition, record amount of HCl added, pH, and observations of solution.

8. Continue additions until pH returns to starting value. Post Lab Questions

1. How was the solubility of he protein (casein) related to the pH of the solution? 2. At what pH was the most precipitate formed? 3. What caused the change in solubility?


Protein Sequence of Casein

Protein Sequence of Insulin


LLaabb RReefflleeccttiioonn EEssssaayy Write a four paragraph essay reflecting on the lab procedure, lab observations,

your knowledge of the lab, and ways you could have improved this lab experience. Use the outline below as a guide for 4 paragraphs.

Lab Overview

Describe/summarize the procedure

What was performed during the lab? What materials were used?

What role did each group member have? Lab Observations Overview

Describe what was observed. Describe how the observations indicate what was being studied

What do the observations tell you? How are the observations used to prove/disprove the objective of the lab?

Lab Content Connection

Describe the lecture principles to the lab What was occurring during the lab How do the lecture/POGIL activities tie in with the lab principles being

studied. What is the ‘Chemistry’ behind the lab?

Lab Improvement

Describe was the lab could have been performed better.

How could the lab notebook detail more precise information? How could observations during the lab be improved?

What would you change? What improvements could you make? Lab notebook writing? Organization?


Lab Reflection Essay Rubric Category 4 3 2 1

Introduction First paragraph is catch. Thesis is evident and to the point regarding lab.

First paragraph is weak. Thesis is mixed among many sentences and hard to piece together.

A catchy beginning was attempted by confusing. Thesis is not entirely apparent.

No attempt made to catch readers attention. Thesis is not apparent.

Accuracy of Facts

All facts presented accurately and related to lab.

Almost all facts present are accurate. Only occasionally related to lab.

Most facts presented are (70%) accurate. Evidence is suggested regarding lab.

Several factual errors made in essay. No effort to relate to lab.

Organization Essay is well organized. Four paragraphs evident. Essay follows logical order with clear transitions.

Essay is pretty well organized. Four paragraphs evident. Essay is mostly logical with one idea out of place.

Essay is hard to follow. Paragraphs unclear. Essay does not follow logical order.

Ideas seem to be randomly arranged. No effort at paragraph organization.

Focus on Assigned

Topic

Entire essay discusses lab. Allows reader to fully understand lab topic.

Most of essay is related to lab. Essay wanders around one point, but comes back into main focus.

Some of the essay is related to topic, but reader does not learn much about the topic.

No attempt has been made to relate lab.

Mechanics The essay has few, if any spelling, punctuation, capitalization, grammar, or usage errors.

The essay has three or less mechanical errors.

The essay has five or less mechanical errors.

The essay has more than five mechanical errors.

Student____________________ Class________ Total Points_______ Grade______


Carbohydrate Pre class Assignment

Food Table Directions: In the column on the left, identify a food or food product, which contains carbohydrates or proteins. In the middle column, identify if the food contains proteins or carbohydrates. In the final column, identify the purpose as: short-term energy, long-term energy, or repairs/rebuilds tissue. Food Protein or Carbohydrate Purpose


Molecules Essential For Life Carbohydrates

I. Carbohydrates A. Organic Compound 1. Contains atoms of a. Carbon b. Hydrogen c. Oxygen d. ration 1:2:1 B. Used in humans

1. store short term energy for cells 2. store sugar (moderate term) energy

a. in liver for cells C. Groups of Carbohydrates 1. Based on number of repeating units

a. Monosaccharide—simple (single) sugar -‘mono’ = 1 -‘saccharide’ = sugar -glucose b. Disaccharide—double sugar -‘di’ = 2 -‘saccharide’ = sugar -sucrose (table sugar) c. Polysaccharide -‘poly’ = many -‘saccharide’ = sugar- -starch

D. Representation methods of Carbohydrates 1. Fischer projections 2. Hawthorn projections 3. Neumann projections


Carbohydrate Chemistry Laboratory Activity Today, scientists use a combination of biology and chemistry for their understanding of life and life processes. Thus, an understanding of chemistry of living things is necessary. Carbohydrates make up a large group of chemical compounds found in cells. Carbohydrates are an energy source of is used in making cell structures. I. Chemical Tests on Know Carbohydrates Benedict’s Test

� Fill a 500ml beaker half full of water. Bring the water to a boil on a hot plate. The boiling water is called a hot water bath. CAUTION: WATER IS VERY HOT! 1. Number three clean test tubes one to three, place group initials on each 2. Using a clean eye dropper, add the following to each tube (use Figure 6-

3 as a guide) i. TUBE 1—30 drops of monosaccharide solution ii. TUBE 2—30 drops of disaccharide solution iii. TUBE 3—30 drops of polysaccharide solution

3. Add 30 drops Benedicts solution to each test tube using a separate eye- dropper. CAUTION: If Benedict’s spillage occurs, rinse with water an call your teacher immediately

4. Record initial color observations of test tubes and mark in Table 6-1 column marked “color of solution + Benedicts”

5. Place the three test tubes into the hot water bath for five minutes. 6. After 5 minutes, use a test tube holder to remove the tubes from the hot

water bath CAUTION: Water and test tube are very hot. Handle test tubes only with a test tube holder.

7. Observe any color changes in the solutions. NOTE: A color change may or may not occur when Benedict’s solution is added to a carbohydrate and heated. A change from blue to green, yellow, orange, or red occurs if a monosaccharide is present. The original blue color will remain after heating if a disaccharide or polysaccharide is present.

8. Record color observations in table 6-1 in the column marked “Benedict’s color after heating.


Iodine Test

� Clean and rinse test tubes 1-3 1. Using a clean eye dropper, add the following to each tube (use

Figure 6-4 as a guide) i. TUBE 1—30 drops of monosaccharide solution ii. TUBE 2—30 drops of disaccharide solution iii. TUBE 3—30 drops of polysaccharide solution

2. Add 4 drops of iodine solution to each tube. CAUTION: If iodine spillage occurs, rinse with water and call your teacher immediately.

3. Observe any color changes in the solutions. NOTE: A color change may or may not occur when iodine solution is added to a carbohydrate. A change from its original rust color to deep blue-black occurs if a polysaccharide is present. The original color of the carbohydrate remains if a disaccharide or monosaccharide sugar is present.

4. Record color observations in table 6-1 in the column marked “Iodine color after”

Chemical Tests on Unknown Carbohydrates

Having tested known carbohydrates, you are now ready to test some unknown

substances. By comparing results of the Benedict’s and iodine tests in Table 6-1,

you should be able to classify known substances as monosaccharide,

disaccharides, or polysaccharides.

1. Number 5 clean test tubes 1-5 and include your group initials.

2. Add the following to each test tube using a clean eye dropper for each (use

Figure 6-5 as a guide)

o TUBE 1—20 drops honey solution

o TUBE 2—20 drops liquid oats

o TUBE 3—20 drops table sugar solution

o TUBE 4—20 drops apple juice solution

o TUBE 5—20 drops powdered sugar solution

3. Add 30 drops of Benedict’s solution to each test tube.

4. Place all 5 test tubes into a hot water bath for 5 minutes.

5. Remove the test tubes from the bath with a test tube holder and note any

color changes. Recorded the color of the solutions in Table 6-2.

6. Rinse and clean all test tubes.


7. Add the following to each test tube using a clean eye dropper for each (use

figure 6-6 as a guide)

o TUBE 1—20 drops honey solution

o TUBE 2—20 drops liquid oats

o TUBE 3—20 drops table sugar solution

o TUBE 4—20 drops apple juice solution

o TUBE 5—20 drops powdered sugar solution

8. Add 4 drops iodine solution to each tube.

9. Note any color changes and record in Table 6-3

On the basis of your results, classify each carbohydrate as a monosaccharide,

disaccharide or polysaccharide and record answers in Table 6-3.

TABLE 6-1

Test Tube Number

Carbohydrate Type

Color of solution + Benedict’s

Change in color after heating with Benedicts

Change in color after

adding iodine 1

Monosaccharide

2

Disaccharide

3

Polysaccharide

TABLE 6-2 Carbohydrate Benedicts

Color after heating

Iodine Color Type of Carbohydrate

Honey

Oats

Sugar

Apple Juice

Powdered Sugar


Analysis 1. Name the three categories of carbohydrates studied in this investigation.

2. What three elements are present in all carbohydrates?

3. Give two examples each of sugars that are:

a. monosaccharide

b. disaccharides

c. polysaccharides

4. How many times larger is the number of hydrogen atoms than oxygen atoms in all carbohydrates?

5. “Mono-“ means one, “di” means two, “poly” means many. Why are these terms used in describing the three types of sugars?

6. How can you tell by using Benedict’s and iodine solutions if a sugar is a:

a. monosaccharide

b. disaccharide

c. polysaccharide

7. A certain sugar has no change in color when tested with Benedict’s solution.

a. Can you tell why type of saccharide it is?

b. Explain. 8. A certain sugar has a color change in Benedict’s solution.

a. Can you tell why type of saccharide it is?

b. Explain.

9. Give an example of a food that is a:

a. monosaccharide

b. disaccharide

c. polysaccharide


Initial Question Can the makers of Splenda® use the advertising slogan “Tastes like sugar

because it is made from sugar?”—Federal lawsuit filed 11/2004

Existing Information Carbohydrates

• Monosaccharides/Disaccharides Synthetic molecules as sweeteners

• Aspartame/Sucralose/Saccharin Molecular Structures

• Reactivity of m-,o-,p- positions

Reflect and Organize Students may ask for further information or clarification on the following topics. • What is the basis of the lawsuit?

o Is this a valid point? • Structure of sucralose? • Synthesis of sucralose? • Structure of aspartame? • Synthesis of aspartame? • Taste regions of sucralose? • Principles of advertising?

TThhee PPeennnn IInnssttrruuccttiioonnaall MMooddeell Topic: Production of artificial sweeteners and advertising.

New Information Needed? Students will be given handouts of information regarding:

• Synthesis of Sucralose—U.S. Patent office

• Background information about Sucralose

• Background information about Aspartame

•

Results Students will come to the conclusions that there are a few methods for the production of sucralose. They may agree or disagree that the lawsuit is valid. Students will be asked to support their arguments/opinions with supporting evidence.

Community Knowledge The advertising slogan used by Splendad®, “Tastes like sugar because it is made from sugar” is highly controversial and recently contested in court by the makers of Equal (aspartame). One of the main reactants in the U.S. patent for the production of sucralose is sucrose. The U.S. patent also discusses other methods of producing Splenda® from sucrose derivatives. It is unclear which method the makers of Splenda® use for the cost efficient and bountiful production of Splenda®.

Peer Review Students will share their results and opinions of the lawsuit. The actual verdict will then be handed out, read, and discussed. Student opinions and reactions will be generated.

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United States Patent 4,801,700 Tully , et al. January 31, 1989

Process for the preparation of 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4-chloro-4-deoxy-.alpha. Inventors: Tully; William (Dublin, IE), Vernon; Nicholas M. (Dublin, IE), Walsh; Peter A. (Blackrock, IE) BACKGROUND OF THE INVENTION This invention relates to a process for the preparation of 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4-chloro-4-deoxy-.alpha. -galactopyranoside. This compound is a potent sweetener, having a sweetness several hundred times that of sucrose. Its use as a sweetener and in sweetening compositions is disclosed in U.S. Pat. No. 4,435,440. The preparation of 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4-chloro-4-deoxy-.alpha. -galactopyranoside or as it is sometimes referred to in the literature, 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose, (hereinafter referred to as "sucralose") involves the substitution of chlorine atoms in the sucrose molecule in one of the five secondary hydroxyl positions and in two of the three primary hydroxyl positions. This particular selection of positions usually means that any synthetic route must involve the preparation of an intermediate sucrose derivative having the required positions available for chlorination while the other positions are blocked. In particular, the reactive 6-position must not be chlorinated, while the 4-position must be rendered available for chlorination. One route proposed in the literature (Fairclough et al, Carbohydrate Research 40 (1975) 285-298) involves the formation of the 6,1',6'-tritrityl derivative of sucrose, peracetylation of the molecule and then detritylation with migration of the 4-acetyl radical to the 6-position, to give 2,3,6,3',4'-penta-O-acetylsucrose which has the correct hydroxy groups unprotected. Subsequent reaction with a chlorinating agent provides the 4,1',6'-trichlorogalactosucrose penta-acetate which in turn yields sucralose on removal of the acetyl groups. The chlorination proceeds with inversion of configuration at the 4-position. The 1' and 6'-positions freely rotate, but the 4-position cannot and the glucose ring is thus inverted at the 4-position yielding a galactose derivative so that the product is a galactosucrose. Another route is set forth in U.S. Pat. No. 4,380,476 and comprises the steps of: (a) reacting sucrose with an acylating reagent under conditions to provide a mixture of acylated sucrose derivatives containing a major proportion of 6-monoacylated material; (b) optionally separating the 6-monoacylated sucrose derivative from other acylated derivatives before step (c); (c) reacting the monoacylated sucrose derivative with a chlorinating reagent capable of chlorinating at positions 1', 4 and 6' of a sucrose 6-acylate; and (d) deacylating and separating (in either order) the sucralose material formed. A further process for preparing sucralose is set forth in U.S. Pat. No. 4,362,869. This process converts sucrose through a number of steps into sucralose. This process describes the sequential steps of (1) tritylation of sucrose to block the three primary alcohol groups; (2) acetylation of the five secondary alcohol groups as acetates; (3) detritylation of the three primary alcohol groups to deblock them; (4) acetyl migration from the 4-position to the 6-position; (5) chlorinating the desired alcohol groups at positions 4, 1', 6'; and (6) deblocking the remaining five alcohol groups by deacetylation thereby yielding sucralose.



The invention disclosed in U.S. Pat. No. 4,362,869 is centered around the acetyl migration from the 4-position to the 6-position which is effected by treating a solution of 2,3,4,3',4'-penta-O-acetyl sucrose in an inert solvent with a weak acid at an elevated temperature. It was found that selection of specific reaction conditions for the acetyl migration gave considerably higher yields overall for separate detritylation and migration than the prior art which taught a one stage process for these steps. The weak acid utilized is preferably a carboxylic acid, especially an aliphatic carboxylic acid such as acetic acid. It is stated that any acid having an acid strength of the same order as acetic acid under the conditions used will suffice. The reaction temperature should be elevated above ambient temperature in order to provide an acceptable reaction time. A temperature of from about 80.degree. to 150.degree. C. is said to be suitable, preferably 100.degree. to 130.degree. C. The inert solvent is said to be any solvent for penta-O-acetyl sucrose which remains liquid at the elevated temperature selected, e.g. a temperature in the range of 100.degree. to 140.degree. C. Ketonic solvents are particularly preferred, especially methyl isobutyl ketone, which refluxes at about 117.degree. C. A dilute solution of the acid in the solvent is said to be suitable, e.g. a solution of from 2 to 10% by weight, especially about 5%. This degree of dilution is suitable for reaction with the sucrose penta-acetate dissolved at a concentration of up to 30% by weight, e.g. about 20%. Ester solvents of sufficiently high boiling point are also useful, e.g. n-butyl acetate. Also of particular interest are aromatic hydrocarbons such as toluene or xylene. When the reaction is completed, the reaction mixture is cooled an 2,3,6,3',4'-penta-O-acetylsucrose crystallizes. After an additional period of time at 0.degree. C., the crystalline product is filtered, washed and dried and then proceeds to the chlorination step. While an effective process, the above process involves the use of a carboxylic acid at high temperatures in the presence of free hydroxyl groups, conditions known to promote acylation. SUMMARY OF THE INVENTION The foregoing objects and other features and advantages of the present invention are achieved by an improved process for the preparation of sucralose. This process comprises the steps of (1) tritylation of sucrose to block the three primary alcohol groups; (2) acetylation of the five secondary alcohol groups as acetates; (3) detritylation of the three primary alcohol groups to deblock them; (4) acetyl migration; (5) selective chlorination; and (6) deacetylation to deblock the remaining alcohol groups to yield sucralose.


Equal, Splenda Settle Lawsuit Over Ad Claims By MARYCLAIRE DALE The Associated Press Journal and Courier 5/11/NEWS PHILADELPHIA - The makers of Splenda and Equal on Friday settled a lawsuit over Splenda's disputed advertising slogan - "Made from sugar so it tastes like sugar." The settlement came after the jury announced that it had reached a verdict. Merisant Co., which makes Equal, accused Splenda of confusing consumers into thinking its product was healthier and more natural than other artificial sweeteners. Splenda's marketer, McNeil Nutritionals, countered that it simply has a better product backed by superior advertising. A McNeil spokeswoman in the courtroom said the amount of the settlement wouldn't be announced. The two sides planned to issue a joint statement later Friday. Chicago-based Merisant was seeking more than $200 million from McNeil - at least $183 million for unfair profits since 2003 and compensation for at least $25 million in lost sales. The active ingredient in Splenda starts as pure cane sugar but is chemically altered to create a compound that contains no calories, according to McNeil. The final product contains no sugar. The one-month trial focused mostly on Splenda's advertising slogan, but it ended in a settlement after the jury said it had reached a verdict Friday afternoon. Settlement talks began after jurors asked the judge for a calculator and a white board, an indication that they were computing damages to be awarded to Merisant. Lawyers rushed to the courtroom to try to delay the jury's announcement and then huddled in a courthouse meeting room. McNeil's own consultants said its slogan confused potential customers, some of whom thought that Splenda was sugar without the calories, Merisant's attorneys said. McNeil rejected a plan to add the phrase "does not contain sugar" to the front of Splenda's yellow box, which might have cleared up the confusion, Merisant said. Because the manufacturing of Splenda begins with sugar, McNeil can accurately claim that Splenda is "made from" sugar, according to its attorneys. Splenda is used in more than 4,000 food and drink products and is included in recipes at numerous chain restaurants. It had 60 percent of the consumer artificial sweetener market last year, according to the research firm Information Resources Inc. Equal, which comes in blue packets and is made with aspartame, and Sweet'N Low, in pink packets and made with saccharin, each held about 14 percent of the consumer market.


Advertisement Rubric Category 4 3 2 1

Design Advertisement and storyboard are designed effectively. Student shows strong evidence in developing presentation methods.

Advertisement and storyboard are well designed. Student shows evidence in developing presentation methods.

Advertisement and storyboard design is emerging Student shows emerging presentation methods.

No effort in advertisement and storyboard design are apparent.

Creativity Storyboard & advertisement are very creative. No similarity to current advertises.

Storyboard & advertisement are creative. Only slightly similar to current advertise.

Storyboard & advertisement are slightly creative. Similarity to current advertises exists.

No effort in creativity or individuality has been made.

Organization Advertisement is well organized. Storyboard follows logical order with clear transitions.

Advertisement is pretty well organized. Storyboard is mostly logical with one idea out of place.

Advertisement is hard to follow. Storyboard does not follow logical order.

Ideas seem to be randomly arranged. No effort at Advertisement & storyboard organization.

Focus on Assigned

Topic

Entire advertisement and storyboard are focused on product and company.

Advertisement and storyboard are primarily focused on product and company.

Advertisement and storyboard are partically focused on product and company.

No attempt has been made to focus advertisement.

Mechanics The essay has few, if any spelling, punctuation, capitalization, grammar, or usage errors.

The essay has three or less mechanical errors.

The essay has five or less mechanical errors.

The essay has more than five mechanical errors.

Student____________________ Class________ Total Points_______ Grade______


LESSON ASSESSMENT QUESTIONS 1. Describe the structural differences between primary, secondary, tertiary, and

quaternary proteins.

2. Explain how many different types of atomic interactions cause folding patterns in proteins.

3. How can the sequence of amino acids determine the relative properties of a protein?

4. Explain how changes in intercellular or extracellular conditions can affect the structure of proteins. (hint: temperature, pH)

5. Compare and contrast both structural and functional features between proteins and carbohydrates.

6. A friend comes to you and says that they are sick and tired of being thin and scrawny and they want to go on a modified food program to bulk up. Would you recommend carbohydrate loading or protein loading? What are the advantages and disadvantages of each?

7. A clear solution is presented to you. The teacher tells you that it contains a carbohydrate. How can you test to determine which carbohydrate the solution contains?

8. What is the C:H:O atomic ratio for a. Monosaccharides? b. Disaccharides?

9. Using the chemical formula C6H12O6 (any straight chain, structural isomer is acceptable), draw a

a. Neumann projection looking down C2. b. Hawthorn projection looking down C2. c. Fischer projection.

10. What are the differences between carbohydrate sweeteners, low calorie sweeteners, and no calorie sweeteners?


References “Acid-Base Properties of Proteins.” Chemistry; A Project of the American Chemical

Society. Freeman. New York, 2005; 619-621. Cambell, Neil, A. “Carbohydrates.” Biology; 3rd Edition. The Benjamin/Cummings

Publishing Company, Inc. 1993: 190-199 Dale, MaryClair. “Equal, Splenda Settle Lawsuit Over Ad Claims. ”The Associated

Press Journal and Courier. 5/11/07 Garrett, R. H., and Grisham, C.M. Principles of Biochemistry with a Human Focus,

updated Third Edition. Brooks/Cole. Belmont, CA, 2007. Greenberg, Rae, Groves, Merton, L., Dower, Harold, J. “Human β-Casein.” The Journal of

Biological Chemistry. 1984; 259, 8: 5123-5138.

Marieb, Elaine, N. “The Chemical Senses: Taste and Smell.” Human Anatomy and Physiology, 2nd Ed. Benjamin Publishing Company. New York, 1992; 496-499.

McMurry, John., and Casellion, Mary, E. “Acid-Base Properties of Amino Acids.”

Fundamentals of General, Organic, and Biological Chemistry; Fourth Edition. Pearson Education, Inc. New Jersey. 2003; 506-509.

Tully; William, Vernon; Nicholas M., Walsh; Peter A. “Process for the preparation of 1,6-

dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4-chloro-4-deoxy-.alpha. United States Patent 4,801,700; January 31, 1989

jeffrey t. kushner chem 508 protein/carbohydrate ...kushnert/508/kushner_thesis_lessonplan.pdfthe...

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