Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 23, Problem 29P
What acyl groups have we seen transferred by reactions thiamine pyrophosphate as a coenzymes? (Hint: See problems 9, 10, 11, 27, and 28.)
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The dynamic process by which both forms of a- and B-D-glucopyranose in solution change slowly into an equilibrium mixture of both is known as
(choose the name).
OH
OH
Но
но
НО
HO
OH
OH
OH
OH
a-D-glucopyranose
36%
B-D-glucopyranose
64%
OA Acetylation
O B. Enediol Rearrangement
OC Mutarotation
O D. Acetal Formation
O E Epimerization
Please draw by hand. Triosephosphate isomerase (TIM) catalyzes the conversion of dihydroxyacetone phosphate to glyceraldehyde-3-phosphate. The enzyme's catalytic groups are Glu 165 and His 95. In the first step of the reaction, these catalytic groups function as a base and an acid catalyst, respectively. Propose a mechanism for the reaction.
ОН
2-03Р0
ОН
dihydroxyacetone phosphate
triosephosphate isomerase
2-03РО.
H
glyceraldehyde-3-phosphate
FYI Glu is glutamic acid and his is histadine
One of these reactions is a reductive amination.
Write the oxidation states ( a number) next to each boxed carbon.
Which reaction is a reductive amination? A or B
Identify the oxidized and reduced states of the coenzymes
Chapter 23 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 23.1 - Prob. 2PCh. 23.1 - Prob. 3PCh. 23.2 - How many conjugated double bonds are there in a....Ch. 23.2 - Instead of adding to the 4a position and...Ch. 23.2 - Prob. 7PCh. 23.3 - Prob. 8PCh. 23.3 - Acetolactate synthase is another TPP-requiring...Ch. 23.3 - Acetolactate synthase transfers the acyl group of...Ch. 23.3 - Prob. 12PCh. 23.5 - Which compound is more easily decarboxylated?
Ch. 23.5 - Prob. 14PCh. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - The enzyme that catalyzes the C C bond cleavage...Ch. 23.5 - Propose a mechanism for the ,-elimination reaction...Ch. 23.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 23.6 - Prob. 20PCh. 23.7 - How do the structure of tetrahydrofolate and...Ch. 23.7 - What is the source of the methyl group in...Ch. 23.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 23 - How does the metal ion in carboxypeptidase A...Ch. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - For each of the following reactions, name both the...Ch. 23 - Prob. 27PCh. 23 - When transaminated, the three branched-chain amino...Ch. 23 - What acyl groups have we seen transferred by...Ch. 23 - Propose a mechanism for the following reaction:Ch. 23 - Draw the products of the following reaction, where...Ch. 23 - When UMP is dissolved in T2O, exchange of T for H...Ch. 23 - Dehydratase is a PLP-requiring enzyme that...Ch. 23 - In addition to the reaction mentioned in Section...Ch. 23 - PLP can catalyze both ,-elimination reactions...Ch. 23 - The glycine cleavage system is a group of four...Ch. 23 - Prob. 37PCh. 23 - FADH2 reduces , -unsaturated thioesters to...
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- One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose 5-phosphate with ribose 5-phosphate in the presence of a transketolase to give glyceraldehyde 3-phosphate and sedoheptulose 7-phosphate. (a) The first part of the reaction is nucleophilic addition of thiamin diphosphate (TPP) ylide to xylulose 5-phosphate, followed by a retro-aldol cleavage to give glyceraldehyde 3-phosphate and a TPPcontaining enamine. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is addition of the enamine to ribose 5-phosphate followed by loss of TPP ylide to give sedoheptulose 7-phosphate. Show the mechanism.arrow_forwardTriosephosphate isomerase (TIM) catalyzes the conversion of dihydroxyacetone phosphate to glyceraldehyde-3-phosphate. The enzyme’s catalytic groups are Glu 165 and His 95. In the first step of the reaction, these catalytic groups function as a general-base and a general-acid catalyst, respectively. Propose a mechanism for the reaction.arrow_forwardNonearrow_forward
- The vitamin Niacin is used to form nicotinamide adenosine dinucleotide, which readily shuttles between its oxidized (NAD+) and reduced (NADH) forms. The latter serves as a cellular equivalent to NaBH4. The essential portions of the structures are shown below. Outline a mechanism for the cellular conversion of pyruvate to lactate. (Note: like NaBH4, NADH cannot reduce carboxylic acid carbonyls).arrow_forwardIn the body, during the citric acid cycle the following reaction occurs as the first part of an enzyme mediated process. но OH YYYYYY OH OH H₂O NaBH4 LiAlH4 H₂SO4 and heat K₂Cr2O7 HQ OH What reagent would be used to bring about this reaction in the laboratory? OH 3arrow_forwardWhy has triglyceride autooxidation occurred selectively to give the following product? QOH O This peroxide is the most stable option. O That position is the least crowded. O Allylic H atoms are easier to abstract than alkyl. O Oxygen is a selective diradical.arrow_forward
- If an enzyme-catalyzed reaction has a high rate at low pH and low rate at higher pH, this implies that a group on either the enzyme or the substrate must be for an efficient reaction. leaving group oxidoreductase coenzymes O protonated deprotonated The compound that consists of deoxyribose linked by an N-glycosidic bond to N-9 of guanine is: adenylate deoxyguanosine guanosine nucleotide guanylatearrow_forwardDraw the following sugar derivatives. 1,3,6-tri-O-methyl-d-fructofuranosearrow_forwardter 18 em 18.18 Part A What coenzyme picks up hydrogen when a carbon-oxygen double bond is formed? Express your answers as a chemical expression. ΑΣΦ Submit Previous Answers Request Answer X Incorrect; Try Again; 3 attempts remalning ide Feedback (१ ।arrow_forward
- Which coenzyme is responsible for the following reaction? CO,H CO,H OH HO.. ОН ОН ОН O TPP (thiamine pyrophosphate) O NAD* (or NADP*) Ο ΚΗ2 O FADH2 В12 O PLP (pyridoxal phosphate) O one of the THE (tetrahydrofolate) coenzymes O NADH (or NADPH) O biotin O FADarrow_forwardWhat advantage does the enzyme gain by forming an imine?arrow_forwardAcetolactate synthase transfers the acyl group of pyruvate to alpha-ketobutyrate. This is the first step in the biosynthesis of the amino acid isoleucine. Propose a mechanism for this reaction.arrow_forward
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