ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
9th Edition
ISBN: 9781337034623
Author: McMurry
Publisher: CENGAGE C
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Chapter 25.SE, Problem 35MP
Interpretation Introduction
Interpretation:
Suitable mechanisms for the three steps involved in the biosynthesis of L-fucose from GDP-D-mannose shown are to be proposed.
Concept introduction:
Step 1 involves three reactions: i) Oxidation of a secondary alcohol to a
Step 2 involves two epimerization reactions, one involves the acidic site of the enzyme and other involves the basic site of the enzyme.
Step 3 involves attack of NADH on the carbonyl group and protonation.
To propose:
Suitable mechanism for the three steps involved in the biosynthesis of L-fucose from GDP-D-mannose shown.
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Chapter 25 Solutions
ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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- Glucosamine, one of the eight essential monosaccharides (Section 25-7), is biosynthesized as its 6-phosphate derivative from fructose 6-phosphate by reaction with ammonia. Propose a mechanism.arrow_forwardThe carbonyl group in d-galactose may be isomerized from C1 to C2 by brief treatmentwith dilute base (by the enediol rearrangement, Section 23-7). The product is the C4epimer of fructose. Draw the furanose structure of the product.arrow_forwardRaffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose doesnot reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinosegives d-glucose, d-fructose, and d-galactose. When raffinose is treated with invertase,the products are d-fructose and a reducing disaccharide called melibiose. Raffinose isunaffected by treatment with a b@galactosidase, but an a@galactosidase hydrolyzes itto d-galactose and sucrose. When raffinose is treated with dimethyl sulfate and basefollowed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetraO-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the completestructures of raffinose and melibiose, and give a systematic name for melibiose.arrow_forward
- Trehalose is a nonreducing disaccharide (C12H22O11) isolated from the poisonous mushroom Amanita muscaria. Treatment with an a@glucosidase converts trehalose to two molecules of glucose, but no reaction occurs when trehalose is treated with a b@glucosidase.When trehalose is methylated by dimethyl sulfate in mild base and then hydrolyzed,the only product is 2,3,4,6-tetra-O-methylglucose. Propose a complete structure andsystematic name for trehalose.arrow_forwardThe dehydration of citrate to yield cis-aconitate, a step in the citric acid cycle, involves the pro-R “arm’’ of citrate rather than the pro-S arm. Which of the following two products is formed?arrow_forward
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