The Kiliani–Fischer reaction for the synthesis of epimeric aldoses is to be outlined and Fischer projection of D − ( − ) − Arabinose and D − ( − ) − Ribose is to be represented on the basis of given information. Concept introduction: 舧 A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen-oxygen atom ratio of 2:1 舧 HNO 3 is an oxidizing agent. 舧 Carbohydrates are oxidized by HNO 3 to give aldaric acid as a product. 舧 Aldaric acids are carbohydrates having two carboxylic acids. They are formed due to oxidation reaction of aldoses with dilute HNO 3 and their general reaction can be represented as: 舧 The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules. 舧 A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active. 舧 The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers. 舧 The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive. 舧 Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive. 舧 The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of the respective aldoses, thereby, lengthening the carbon chain of the compound. It is an effective and economic process for synthesizing monosaccharides through the hydrolysis of a cyanohydrin. Thus, it lengthens the carbon chain of the aldose by one carbon atom. It is used to produce epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.

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Answer 1

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Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 14PP

Interpretation Introduction

Interpretation:

The Kiliani–Fischer reaction for the synthesis of epimeric aldoses is to be outlined and Fischer projection of D−(−)−Arabinose and D−(−)−Ribose is to be represented on the basis of given information.

Concept introduction:

舧 A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen-oxygen atom ratio of 2:1

舧 HNO3 is an oxidizing agent.

舧 Carbohydrates are oxidized by HNO3 to give aldaric acid as a product.

舧 Aldaric acids are carbohydrates having two carboxylic acids. They are formed due to oxidation reaction of aldoses with dilute HNO3 and their general reaction can be represented as:

舧 The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules.

舧 A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.

舧 The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.

舧 The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

舧 Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.

舧 The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of the respective aldoses, thereby, lengthening the carbon chain of the compound. It is an effective and economic process for synthesizing monosaccharides through the hydrolysis of a cyanohydrin. Thus, it lengthens the carbon chain of the aldose by one carbon atom. It is used to produce epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.

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Identify monomeric and multimeric (di-,tri-meric, for example) saccharides from this group. If you come across multimeric polypeptides, state the mono- mers that form these multimers. State the nature of the bond that links two units together in each case. (a) Maltose (b) Trehalose (c) Lactose (d) Sucrose (e) Cellobiose (f) Agarose

Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.

A tripeptide contains lysine (R= -(CH₂)4NH₂), phenylalanine (R= -CH₂C6H5) and glycine (R= -H). It was found that the tripeptide reacts with 2 moles of DNFB to give compound A. When compound A was treated with SOCI2, glycine was activated. When hydrolyzed, both NH₂ groups of lysine were found to be DNP-labelled. What is the structure of the tripeptide? Select one: H (CH₂)2NH2 CH NH CH H₂N O O H₂N H₂N H₂N C (CH2)4NH2 CH 010 (CH2)4NH2 CH C=O CH,Ph CH NH NH NH CH CH,Ph CH H 010 CH CH,Ph CH (CH2)4NH2 ΝΗ NH NH NH CH,Ph CH H CH COOH H CH COOH COOH COOH

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 14PP

Interpretation Introduction

Interpretation:

The Kiliani–Fischer reaction for the synthesis of epimeric aldoses is to be outlined and Fischer projection of D−(−)−Arabinose and D−(−)−Ribose is to be represented on the basis of given information.

Concept introduction:

舧 A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen-oxygen atom ratio of 2:1

舧 HNO3 is an oxidizing agent.

舧 Carbohydrates are oxidized by HNO3 to give aldaric acid as a product.

舧 Aldaric acids are carbohydrates having two carboxylic acids. They are formed due to oxidation reaction of aldoses with dilute HNO3 and their general reaction can be represented as:

舧 The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules.

舧 A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.

舧 The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.

舧 The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

舧 Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.

舧 The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of the respective aldoses, thereby, lengthening the carbon chain of the compound. It is an effective and economic process for synthesizing monosaccharides through the hydrolysis of a cyanohydrin. Thus, it lengthens the carbon chain of the aldose by one carbon atom. It is used to produce epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 14PP

Interpretation Introduction

Interpretation:

The Kiliani–Fischer reaction for the synthesis of epimeric aldoses is to be outlined and Fischer projection of D−(−)−Arabinose and D−(−)−Ribose is to be represented on the basis of given information.

Concept introduction:

舧 A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen-oxygen atom ratio of 2:1

舧 HNO3 is an oxidizing agent.

舧 Carbohydrates are oxidized by HNO3 to give aldaric acid as a product.

舧 Aldaric acids are carbohydrates having two carboxylic acids. They are formed due to oxidation reaction of aldoses with dilute HNO3 and their general reaction can be represented as:

舧 The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules.

舧 A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.

舧 The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.

舧 The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

舧 Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.

舧 The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of the respective aldoses, thereby, lengthening the carbon chain of the compound. It is an effective and economic process for synthesizing monosaccharides through the hydrolysis of a cyanohydrin. Thus, it lengthens the carbon chain of the aldose by one carbon atom. It is used to produce epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22, Problem 14PP

Interpretation Introduction