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Photosynthesis O O O O OH O OH O OH O H 2 N O Venturicidin A

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Page 1: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

Photosynthesis

!"#$%&

'(()#*%)%+#&(),-")#*%)%+#&()

./0$#$10&2"

3/40&5$670-%)(

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8!"#$

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!)80/.<18&=&)

!(./.010/+2345).&:3789+)+&:/(;

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)

=AB

*+66+?.@=&A+?B</80+

8

9*CABD9*CABD:

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E*:<

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3/40&5$670-%)(

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O

O

O

O

OH

O OH O

OH

O

H2N

O

Venturicidin A

Page 2: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

Calvin Cycle and Carbon Fixation Ribulose

1,5-Bisphosphatecarboxylase/oxygenase

(RuBisCO)

Phosphoglyceratekinase

ATP(x2)

Ribulose1,5-Bisphosphate

3-Phosphoglycerate(x2)

ADP(x2)

1,3-Bisphospho-glycerate(x2)

CO2

Glyceraldehyde3-Phosphate

(x2)

Ribulose5-Phosphate

NADPH(x2)

NADP(x2)

ATP

ADP

SeveralHexoseMonosphosphatePathway-likeReactions

CO2

Ribulose5-PhosphateKinase

Glyceraldehyde3-PhosphateDehydrogenase

Carbon fixation

Carbon assimilation

Ribulose-1,5-BisphosphateRegeneration

Ribulose-1,5-Bisphosphate Carboxylase/Oxygenase (Rubisco) Carboxylase activity

H2OH2C

CO

CH OH

CH OH

H2C O

O

PO O

PO O

O

O

Ribulose1,5-bisphosphate

HH2C

CO

C OH

CH OH

H2C O

O

PO O

PO O

O

O

Enediolintermediate

O C

H+

OH2C

CHO

C O

CH OH

H2C O

O

PO O

PO O

O

O

-Ketoacidintermediate

CO

C O

CH OH

H2C O

PO O

O

O

3-Phosphoglycerate

OH2C

CHO

C OH

CH OH

H2C O

O

PO O

PO O

O

O

Hydratedintermediate

CO

O

HO

C O

CH OH

H2C O

PO O

O

O3-Phosphoglycerate

Page 3: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

Carbon Assimilation

2 x NADP+

2 x Pi

C

C

CH2 O

OH

OHH

PO O

O

2 x Glyceraldehyde

3-phosphate

O

PO O

O

C

C

CH2 O

O

OHH

PO O

O2 x

1,3-Bisphospho-glycerate

Glyceraldehyde-3-phosphate

dehydrogenase

2 x ATP 2 x ADPO

C

C

CH2 O

O

OHH

PO O

O

2 x3-Phospho-glycerate

Phosphoglyceratekinase

H2C

CO

CH OH

CH OH

H2C O

O

PO O

PO O

O

O

Ribulose1,5-bisphosphate

H2O+ CO2

Rubisco

2 xNADPH

=#-H"$2)FIJ>+621/$21/&")

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34,-(),-.'*5+6.)*

ABD EF!

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M)1<+68)?+(1?+L,J(.0J(8/+

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Page 4: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

HOO

OH

OH

O

CH2

n

HOO

OH

OH

O

CH2

O

OH

OH

CH2

( -1,4-glucoside polymerwith -1,6-glucoside

branches)

-1,4-Glucoside bond

-1,6-Glucosidebond

Starch (amylopectin)

O

HOO

OH

OH

OH

CH2

HOO

OH

OH

OH

CH2

O

Dihydroxyacetonephosphate

Triose phosphateisomerase

Transaldolase

Fructosebisphosphatase

Phospho-glucomutase

ADP-glucosepyrophosphorylase

Starchsynthase

Fructose-6-phosphate

P

O

O

O O O

O

OH

CH2

OH

CH2 OH

P

O

O

O OO OH

OH

OH

OH

CH2

Glucose-6-phosphate

PhosphoglucoisomeraseFructose-1,6-bisphosphate

P

O

O

O OP

O

O

O O O

O

OH

CH2

OH

CH2

H H

HOO

OH

OH

OH

CH2

C

C

CH2 O

OH

OHH

PO O

O

Glyceraldehyde3-phosphate CH2

C

C

O

O

HO H

PO O

O

H

Pi

O P

OH

O

OH

-Glucose-1-Phosphate

O

O

OHOH

CH2O

N

N N

N

NH2

P

O

O

AdenosineTriphosphate(ATP)

P

O

O

O

O

OCH2O

N

N N

N

NH2

P

O

O

ADP-Glucose

P

OH

O

O

P

O

O

OOP

O

O

OP

O

O

O

Pyrophosphate

HOO

OH

OH

OH

CH2

HOO

OH

OH

O

CH2

n

OH OH

HOO

OH

OH

OH

CH2

HOO

OH

OH

O

CH2

n

HOO

OH

OH

O

CH2HOO

OH

OH

OH

CH2

ADP

Starch

Page 5: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

ATP/Reducing Equivalent and Triose Transport

Chloroplast Inner Membrane

3-Phospho-glycerate

1,3-Bisphospho-glycerate

Dihydroxyacetonephosphate

Glyceraldehyde3-phosphate

NADP+ Pi

NADH ATPADP

Triose phosphateisomerase

Phosphoglyceratekinase

Glyceraldehyde3-phosphate

dehydrogenase

NAD+ Pi

Triose phosphate/PhosphateExchanger

Triose phosphate/PhosphateExchanger

Pi

Pi

Pi

Pi

3-Phospho-glycerate

1,3-Bisphospho-glycerate

Dihydroxyacetonephosphate

Glyceraldehyde3-phosphate

NADPH ATPADP

Phosphoglyceratekinase

Glyceraldehyde3-phosphate

dehydrogenaseTriose phosphate

isomerase

Cytosol

Stroma

Glycolysis

Sucrose synthesis

HO

O

OH

OH

OH

CH2

HO O

O

OH

CH2

CH2 OH

H

O

-D-Fructofuranoside

-D-Glucopyranosyl

Sucrose(1- -D-glucopyranosido--D-fructofuranoside

Page 6: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

Rubisco (Oxygenase Reaction)

H2C

CO

CH OH

CH OH

H2C O

O

PO O

PO O

O

O

Ribulose1,5-bisphosphate

HH2C

CO

C OH

CH OH

H2C O

O

PO O

PO O

O

O

Enediolintermediate

H2C

CHO

C O

CH OH

H2C O

O

PO O

PO O

O

O

Hydroperoxyintermediate

O OO OH

H+ H2C

C

O

PO O

O

O

C O

CH OH

H2C O

PO O

O

O

O

Phosphoglycolate

3-Phosphoglycerate

9*D/$21/$O04H$0&")

9*,9*<*A3D .,9*<*ABD

E>D/$21/$O04H)#&")!(./.6+0J=68/=.&3!8/(781

H2C

C

O

PO O

O

O

O

Phosphoglycolate

H2C

C

OH

O

O

Glycolate

H2C

C

OH

O

O

Glycolate

O2 H2O2

Glycolateoxidase

HC

C

O

O

O

Glyoxalate

CH2C O

O

Glycine

NH3CH2

C O

O

Glycine

NH3

CH2

C O

O

Glycine

NH3

+

NAD

NADH+ NH3+ CO2

CH

C O

O

Serine

NH3H2C

Glycinedecarboxylase

Serineaminotransferase

C

C O

O

Hydroxy-pyruvate

H2C

OC O

CH OH

H2C O

PO O

O

O

3-Phosphoglycerate

C O

CH OH

H2C OH

O

Glycerate

NAD NADH

-Hydroxyacidreductase

MitochondrionPeroxisomeChloroplast

C O

CH OH

H2C OH

O

Glycerate

Glyceratekinase

ATPADP

OHOH

CH

C O

O

Serine

NH3

H2C

OH

Phosphoglycolatephosphatase

Page 7: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

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Page 8: 0$#$10&2 - Rose-Hulman Institute of Technologybrandt/Chem331/Carbon_fixation_handout.pdfCalvin Cycle and Carbon Fixation Ribulose 1,5-Bisphosphate carboxylase/oxygenase (RuBisCO)

CH2CHO

CH OH

CH OH

H2C OH

2-Carboxyarabinitol-1-phosphate

C

O

PO O

O

O

O

CH2CHO

C O

CH OH

H2C O

PO O

PO O

O

O

-Ketoacidintermediate

CO

O

O

M-+62H$TM-UD

A3D

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ABD

M-+62H$V429GF C:E< V429GF C:E<

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