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 ketone by NAD + . ii) Dehydration to an enone iii) 1,4-Addition of NaDH to the enone iv) Protonation and loss of NAD + . 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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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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 ketone by NAD⁺. ii) Dehydration to an enone iii) 1,4-Addition of NaDH to the enone iv) Protonation and loss of NAD⁺.

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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1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.

What glycosides are formed when each monosaccharide is treated with CH3CH2OH, HCl: (a) β-D-mannose; (b) α-D-gulose; (c) β-D-fructose?

A. Classify each of the following monosaccharides as aldose or ketose. (a) H. (b) CH2OH (c) CH2OH (d) H. C=0 C=0 HO-C-H H-C-H H-C-OH HO-C-H H-C-OH H-C-OH H-C-OH HO-C-H CH2OH H-C-OH CH2OH H-C-OH | CH2OH CH2OH Threose Ribulose Tagatose 2-Deoxyribose

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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 ketone by NAD⁺. ii) Dehydration to an enone iii) 1,4-Addition of NaDH to the enone iv) Protonation and loss of NAD⁺.

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.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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 ketone by NAD⁺. ii) Dehydration to an enone iii) 1,4-Addition of NaDH to the enone iv) Protonation and loss of NAD⁺.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 25.SE, Problem 35MP

Interpretation Introduction