© Macmillan Learning95DECHhGlycolysis intermediateOther compound2-H-C-O-PO3C=OHO-C-HHHO.-CH2OHOHMAnswer Banka five-carbon phosphorylated compoundCooCH₂MacBook ProfructoseResources203PO,-20₂ PO-CH₂H₂C-OPOO-OHOHOHA00Σ

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Answered: © Macmillan Learning 95 DEC H h…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 41MP

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N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne
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H-C -OH CH₂OPO₂²- 3-phosphoglycerate ATP ADP Arrow-pushing Instructions AC XT H-C-OH :O: CH₂OPO3²- =C² H-C-OH -O OPO3² Enz-SH 3 CH₂OPO3²- 1,3-bisphosphoglycerate ADP PO S-Enz H-C-OH CH₂OPO3²- One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. [Enzyme-bound thioester] NADH/H* NAD*, Enz-SH H H-C-OH CH₂OPO3²- Glyceraldehyde 3-phosphate :Ö: H-C-OH CH₂OPO3²- ADP 29
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Isomerization of glucose 1-phosphate to glucose 6-phosphate is energetically favorable. At 37°&delta G° = –1.42 log10K deltaG° = –1.74 kcal/mole at 37°C?
Isoleucine, another of the twenty amino acids found in proteins, is metabolized by a pathway that includes the following step. Propose a mechanism.
rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- glyceraldehyde 3-phosphate Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate. To simplify the drawing process, substitute the structure below for the enzyme-bound thioester. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…
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© Macmillan Learning 95 DEC H h Glycolysis intermediate Other compound 2- H-C-O-PO3 C=O HO-C-H H HO. -CH2 OH OH M Answer Bank a five-carbon phosphorylated compound Coo CH₂ MacBook Pro fructose Resources 203PO, -20₂ PO-CH₂ H₂C-OPO O-OH OH OH A 00 Σ