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 32P
When UMP is dissolved in T2O, exchange of T for H occurs at the 5-position. Propose a mechanism for this exchange. (T=3H; see Problem 31)
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When UMP is dissolved in T2O, exchange of T for H occurs at the 5-position. Propose a mechanism for this exchange.
Provide an electron pushing mechanism for the conversion shown below. Abbreviate the enzyme catalyst
active site groups (BH* and B:) as needed. Which purine base is used?
NH₂
Enz
H₂O
'N
NH
Fill in the missing structures and add curved arrows to show the mechanism of glycoside formation
below.
Step 1: Oxonium ion formation
НО
НО
НО
ОН
НО-
HO OH
D-glucose
Step 2: Alcohol addition
OH
+
H-OH2
HO
H-OR
or
H-OR
НО
НО
OH
HO
oxonium ion
:ÖH2
:ÖH2
НО
HO
НО
+ H2O
НО
ОН
HO
a B-D-glycoside
OH
НО
OR
OR
an a-D-glycoside
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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