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Page 1: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate
Page 2: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

incjestekli’rrotein

ENVIRONMENT

L

/amino acid\

ORGA?lISn

- creatine- porphyrins

acetoacetate,acetyl CoA pyruvate

a-ketoglutsratesuccinyl ConEumarateoxalortcelalc

2 CH 352

Page 3: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH 352 3

Page 4: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

yt J

4 CH 352

Page 5: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH 352 5

Page 6: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

Orni!hine

-A

Ha0

Spocitic ornithine

Argininemembrane transport

Hn( ,,.CtrNI(~COO”SYSte”’:r 1

HOOC-CH

PATP + CO2 + NH:8 + HtO

PADP + P,

6 C H 3 5 2

Page 7: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH 352 7

Page 8: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate
Page 9: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

Acetaldehyde

CoA NAD+ NADH

\ \ fp - - - - - - - - - - - - l; CH,C-S-CoA I

+ a h ; Acetyl-CoAL ____._---L

CH 352

Page 10: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

H O / \ CH,--c-C00Hu --

b4Hydroxyphenyl.

pyruwc acid

O H

CH,COOH

O HHomogentisic acid

HOW-C=C-C-CH,CCH&OOH

Filib b4.M.&J+

acetoacetic acid

CH,HOOCCH,CCH,C--S-&A

bH 1

B-Hydroxy-@-methyl- r - - - - - - - TglUtW+COA ] CH,C--S--Co* ;

Acetoacetic acidI

H--F=C-cooHli

Fumaric acid

10 CH 352

Page 11: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH 352 1 1

Page 12: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

reductase

Dlhydrobioptelin-CH-CH,

I IOH OH

Tulr;lhy~l,olllopla,i”

12 CH 352

Page 13: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH 352 13

Page 14: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH,---C-COO---++

1 4 CH 3 5 2

Page 15: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

H-CCH,CH,CH,CH(NH.)COOH A____* HOOCCH,CH,CH,CCOOH

H,o.w.DP+ transamination d

ho* ~,’ I WY\--S-A j

L-‘)-‘)-----J~a-Aminoadipic ac,d o-Ketoadyc

semaldehyde a c i d AC.StOKX~tl.l-COA

acetoacetyl CoA

CH 352 15

Page 16: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

‘kuknf?du, Twr”nu (proline), ~ST#W (histidine), ntpfh uampruw

Glutamic acidArginine

Hz0Omithine a-Keto&tarsle y-semialdehyde

&N-C-NHCH,CH,CH,CH(NH,)COOH + H,NCH,CH,CH,CH(NH,)COOH -\- H-C-CH,CH,CH(NH,~C~~H

A’-Pyrmline 5-carbaxylic acid I Glutamic acid

5-Formimino-FH,

I b II III u-Ketoglutarate ’&---- - ----I

1 6 CH 352

Page 17: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH,--S-CH,CH,CH(NH,)COOH

CH,CH,CCOOM

8

a-KetobutyrK acid

1, :z.-::,,; 9

CoA.NA”* CO,,NADH

Imbutyryl-CoA

FAD, H,O

isabutyrylCaA r:

a-Methyibutyryl-CoA

F A D H,O

H.0, NAD’CH,CHCHt-S-GA

ILHLH o-Methyl-’ @hydroxybutyiyL

H-C-CHCOOH

8 LH, M&~lIlldO”iCac,d

wmialdehyde

Methylmalonyl-CoAI

r------4,-___

0/ IIHOOCCH,CH,-C--S-Cal\L_------_-------i

Succmyl-CaA

1 7

Page 18: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

18 CH 352

Page 19: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

fl%V4IU~d6lldU

(nonessential amino acid)

Alanine

Asparagine

Aspartate

Cysteine

Glutamate

Glutamine

Glycine

Proline

S e r i n e

Tyrosine

flNkhilliflU

(essential amino acid)

Arginine*

Histidine’

lsoleucine

Leucine

Lysine

Methionine

Phenylalanine

Threonine

TryptophanJ Valine(*-Qla4~bnwl~~:aua”eJwl9f)

CH 352 I 1 9

Page 20: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

NH, + u-ketoglutarate + NAD(P)H + H+ FIZZ= L-glutamate + NAD(P)+ + H?O

7H,C-CH,

l/HHCn AC,N COOHA’-Pyrrollnescarboxylic

acad

2 0,

. CH 352

Page 21: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

O HH O - I - - 0 - C H , - C H - C O O H

8I

O H 3-PhospheD-

glyceric acid

NADHdehydioyenare

O H

H O - P - 0 - C H , - - C - C O O HI! IIc 0 3.Phosphohydroxy-

pynwic acid

?HHO-A-0-C&-CH-COOH

NH, 3.Phosphoserine

NH,HOOCCHCH,CH,SCH,

Methionine

S-Adenosylmethionine

Methyl-group

1

S-Adenosyl-homocysteine

Homocysteine

HOOCCH(NH,)fW-H- S T.H.CHINH.ICOOH,..jl..l - ---L---k- .

L-Cystathionine

W,N”-methylene- a - K & -butyrate

Cysteine

C H 3 5 2 2 1

Page 22: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

Phenylalanine + NADPH + H+ + 02 + tyrosine + NADP+ + Hz0

2 2 CH 352

Page 23: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

CH 352 23

Page 24: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

24 CH 352

Page 25: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

Threonine

bNH,

a-Ketobutyric acid

W

CHJ-C&OOH

4 AH

a-Acetolacticacid

NAD(P)H

1

reauc,n,i

NAD(P)+

a.@-Dihydroxy-isovaleric acid

bHz0

CH,

l.bCH,- H - C - C O O H

tl

a-Ketoisovalericacid

CH,--CH-CH-COOH

I

Pyruvate ,, (:,, , , ,:.jlll I,,,,.cq

CJ&

CH,-G-COOH

6 bHa-Acetw-hydraxy-

butyric acid

a,&Dihydroxy-0.methylvaleric acid

4

,!/I virlr*ydL.li

H,O2, Ibi i, /:I.,,

W

CH,CH,-C-C-COOH

IL!

a-Ketc+methyl-

valeric acid

u.Keto~sovalericaad

.b

Acetvl-CoA

a-lsopropylmalic

acid

CH,$OOH

CHJHCHCHCOOH ’

OH

P-lsopropylmalicacid

NAD‘5, .l~~.~~yl:n.,i..l~

NADH + co, II ll,. (II ,1>,,3,

W

CH,CHCH>CCOOH

b

a-Ketoisocaproicacid

C H 3 5 2 2 5

Page 26: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

ADP

&Aspartyl phosphate

NADPH

d

arparta,e-remialdehyde

NADP’ dshydrogenare

P,COOH

.N-+H

CH,

r

NADH

4

homn,erme

NAD+dehgdro@masr

COOH

H,N-CH

CH.I -

C&OH

COOH

,,-+

w

CaA1

0-Succinyl-

Aspar t ic

P-semialdehyde

COOH

HzO-,

Cystathionine

CH,Homoserine

W Homocysteine

H C - NH*

COOH

Homoserine phosphoricacid

CY-O--PC&H,Methionine

COOK

n

H,N - C H

HCOH

CH,

Threonine

2 6 CH 352

Page 27: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

HOOC-CH,CH,CHCFHN-Acetylgiutamic

NHCOCH, acid

O H

HO-A-0-CCH&H,CHCOOH

N-Acetyl-

II b 1

y-glutamyl

0 NHCOCH,phosphate

NADPHN- I~vI”I.,-gIO:dm~l

NADP+

4

~l/h\,iilIiP mdilrts\r

P

HCCHgCH,CHCOOH8 I

N-Acetylgiutamic

NHCOCH, v-semialdehyde

.,CP,“,il!“,l,l,,lP

CH,CH,CH,CHCOOHa-N-Acetylomithine

N Y NHCOCH,

H,N CH,CH,CH,CH(NH,)COOH O r n i t h i n e

4& urea cycle

Arginine

H,N-C-NHCH,CH,CH,CH(NH&OOH

CH 352 2 7

Page 28: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

2 8 CH 352

Page 29: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate
Page 30: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

Threoninedeaminase

fi > 4 -Ketobutyric acid+ A+ -+ +-tIsoleucineI II I

D-----+EdY

A&B&c

F-G-Z

nianaEl?xla~:dr~~~l~LLEIElsjOB Go

1. Sequential feedback control

30 CH 352

Page 31: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

r----- --- ----

i D--E--t:c----- --- 7 *

A”‘“4rJI

F‘G-dL---------J

2. Enzyme multiplicity

F----+G------+Z

CH 352 3 1

Page 32: kli’rold-book.ru.ac.th/e-book/c/CH352/ch352-1.pdf · kli’r incjeste rotein ENVIRONMENT L /amino acid\ ORGA?lISn - creatine - porphyrins acetoacetate, acetyl pyruvateCoA a-ketoglutsrate

3. Concerted feedback control

r--------- l--------- 1

A-B-C

?I -> G --) 7

3 2 CH 352