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103Lect3powerpointpdf - Biological Important Nucleophiles...

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Biological Important Nucleophiles and Electrophiles Nucleophiles (electron rich) ROH RO + H + - RSH RS + H + - RNH 3 + RNH 2 + H + Hydroxyl Sulfhydryl Amine HN NH R H + NH N R Imidazole Carbanion usually needs to be stabilized by electron withdrawing group, eg., R 1 = C=O or C=N + + + R 1 R 2 R 3 C H R 1 R 2 R 3 C - H + (HOH) HB pg 8
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+ Electrophiles (electron deficient) H + Proton M=Metal Carbonyl Carbon Carbocation Phosphorus in inorganic phosphate or in phosphoryl groups (eg., in NTPs and dNTPs) Carbon is electronphilic in a cationic amine M n+ C R 1 R 2 O R 1 R 2 R 3 C H R 1 R 2 R 3 C H - OH P O O- -O 1. 2. 3. 4. 5. C R 1 R 2 NH + 6. OR P O O- -O (in aldehydes, ketones, esters, CO 2, ) (carbonium ion) HB pg 8
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H CHO OH H HO OH H OH H CH 2 O O O OH OH H O P O O- P O O- O P O -O O- H N N N N NH 2 Nucleophile Electrophile H H+ GLC ATP The first reaction of glycolysis HB pg 10 Not for E. coli - phosphoryl donor is Phosphoenol pyruvate (PEP)- but same principle
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The first reaction of glycolysis O O OH OH H O P O O- P O O- O P O -O O- H N N N N NH 2 H CHO OH H HO OH H OH H CH 2 O - cont HB pg 10
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The first reaction of glycolysis cont O O OH OH H O P O O- H N N N N NH 2 P O - O - O H CHO OH H HO OH H OH H CH 2 O P O- O O- example of a phosphoryl transfer reaction, a kinase reaction GLC-6-P ADP -PO 3 2- Another way to represent the phosphoryl group HB pg 10 -P i
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H CHO OH H HO OH H OH H CH 2 OH H CHO OH H HO OH H OH H CH 2 OPO 3 2- GLC-6-P GLC ATP ADP CH 2 OH O H HO OH H OH H CH 2 OPO 3 2- ATP ADP CH 2 OPO 3 2- O H HO OH H OH H CH 2 OPO 3 2- CH 2 OPO 3 2- O CH 2 OH H HC OH CH 2 OPO 3 2- + HPO 4 2- NAD + NADH H C OH CH 2 OPO 3 2- O OPO 3 2- ATP ADP H C OH CH 2 OPO 3 2- O - O H C OPO 3 2- CH 2 OH O - O C OPO 3 2- CH 2 O - O C O CH 3 O - O ATP ADP F-6-P DHAP G-3-P 1,3 bisPGA 3-PGA 2-PGA PEP PYR H 2 O 1 2 3 4 5 6 7 8 9 10 on a per glucose basis, from here multiple all by 2 H O OH H OH H OH CH 2 OH OH H O OH H OH H OH CH 2 OPO 3 2- OH ATP ADP 1 2 O 3 POH 2 C OH CH 2 OH H OH H H OH O O 3 POH 2 C OH CH 2 OPO 3 2- H OH H H OH O ATP ADP 3 Fischer projection-open chain Ring form O F-1,6-bisP + H + 1 2 3 4 5 6 1 2 3 4 5 6 1,6 2,5 3,4 Haworth projection Aerobic Glycolysis HB pg 11
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Glycolysis, step 1 Not physiologically reversible- note arrow H CHO OH H HO OH H OH H CH 2 OH H CHO OH H HO OH H OH H CH 2 OPO 3 2- GLC-6-P GLC ATP ADP 1 Kinase Hexokinase In mammalian liver- glucokinase HB pg 11
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Glycolysis, step 2 Intramolecular rearrangment called Isomerization
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