When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of [2-14C]citric acid is formed stereoselectively. Note that citric acid containing only 12C is achiral. Assign an R or S configuration to this enantiomer of [2-14C]citric acid. (Note: Carbon-14 has a higher priority than carbon-12.) C-COOH 14CH,COOH citrate synthase ČH,COOH + 14CH,CSCOA НООС -COH CH,COOH Oxaloacetic acid Acetyl-CoA [2-14C]Citric acid

When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of [2-14C]citric acid is formed stereoselectively. Note that citric acid containing only 12C is achiral. Assign an R or S configuration to this enantiomer of [2-14C]citric acid. (Note: Carbon-14 has a higher priority than carbon-12.) C-COOH 14CH,COOH citrate synthase ČH,COOH + 14CH,CSCOA НООС -COH CH,COOH Oxaloacetic acid Acetyl-CoA [2-14C]Citric acid

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter3: Stereoisomerism And Chirality

Section: Chapter Questions

Problem 3.24P: When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in...

See similar textbooks

Similar questions

Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral α-hydroxy acid A. Identify B and C in the following reaction sequence, and designate the configuration of the enantiomer formed by this route as R or S.
Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.
Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
The first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-Râ€”CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.
Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral αhydroxy acid A. Identify B and C in the following reaction sequence, and designate the conguration of the enantiomer formed by this route as R or S.
Consider the reaction of (E)-hex-3-ene with HBr. Draw the structures for (E)-hex-3-ene and the two major organic products for its reversion with HBr. Show all stereoisomers using wedge and dash stereochemistry at any chirality center
An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.
Assign R or S configurations to each stereogenic center of isoborneol and borneol. Give the relationship between these two stereoisomers.
What are the stereochemical descriptors for mannose and fucose in the above scheme? 1. Both are d-sugars. 2. Both are l-sugars. 3. Mannose is d and fucose is l. 4. Mannose is l and fucose is d.
When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:H+CH3 CH COOH CH3 CH CH3 CH CHOH OHCH2CH3 CH2CH3lactic acidC OOH CH O 3butan-2-ol 2-butyl lactate+(a) Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetriccarbon atom. (Using your models may be helpful.)(b) Determine the relationship between the two stereoisomers you have drawn
What product is formed when the esters in ginkgolide B, the chapter-opening molecule, are hydrolyzed in aqueous acid? Indicate the stereochemistry of all stereogenic centers.
Draw the structural formulas for the first two intermediates formed in the hydrolysis of (1R,2S)-1,2-epoxy-1-methylcyclopentane with aqueous acid. Show stereochemistry if product is a meso compound.