5-Bromouracil causes mutations in DNA. Reason for this should be determined. Concept introduction: A parent DNA molecule consists of two poly nucleotide chains held together by bonds between complementary nitrogen bases. A base is nitrogen containing heterocyclic compound which is found in DNA and RNA. There are mainly five nitrogen bases. (1) Adenine (2) Guanine (3) Cytosine (4) Thymine (5) Uracil In DNA Adenine always makes a double bond with Thymine ( A = T ) and cytosine always makes triple bond with guanine ( G ≡ C ) Enol is a tautomer which exhibiting a special type of functional isomerism namely tautomerism. Tautomerism is a special type of functional isomerism in which isomers are in dynamic equilibrium with each other. Mutation is the process that results in change in the sequence of the DNA, and the compound which causes mutation is known as mutagenic compound.

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Carbohydrates. Determination of the extent of branching in glycogen. The amount of branching (number of α 1⟶ 6 glycosidic bonds) in glycogen can be determined by the following procedure. A sample of glycogen is exhaustively methylated-treated with a methylating agent (methyl iodide) that replaces the hydrogen of every sugar hydroxyl with a methyl group, converting –OH to –OCH3. All the glycosidic bonds in the treated sample are then hydrolyzed in aqueous acid, and the amounts of α -D-2,3-di-O-methylglucopyranose and α -D-2,3,6-tri-O-methylglucopyranose formed are measured. 1- Draw the cyclic structure of α-D-glucopyranose, α-D-2,3-di-O-methylglucopyranose and α-D-2,3,6-tri-O-methylglucopyranose, including the numbering of carbon atoms. 2- Which of α-D-2,3-di-O-methylglucopyranose or α-D-2,3,6-tri-O-methylglucopyranose represents a glucose unit in glycogen which was originally carrying a α 1⟶ 6 glycosidic bond? Explain.

Answer 1

Question

Chapter 26, Problem 36P

Interpretation Introduction

Interpretation:

5-Bromouracil causes mutations in DNA. Reason for this should be determined.

Concept introduction:

A parent DNA molecule consists of two poly nucleotide chains held together by bonds between complementary nitrogen bases.

A base is nitrogen containing heterocyclic compound which is found in DNA and RNA.

There are mainly five nitrogen bases.

(1) Adenine

(2) Guanine

(3) Cytosine

(4) Thymine

(5) Uracil

In DNA Adenine always makes a double bond with Thymine (A=T) and cytosine always makes triple bond with guanine (G≡C)

Enol is a tautomer which exhibiting a special type of functional isomerism namely tautomerism.

Tautomerism is a special type of functional isomerism in which isomers are in dynamic equilibrium with each other.

Mutation is the process that results in change in the sequence of the DNA, and the compound which causes mutation is known as mutagenic compound.

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Carbohydrates. Determination of the extent of branching in glycogen. The amount of branching (number of α 1⟶ 6 glycosidic bonds) in glycogen can be determined by the following procedure. A sample of glycogen is exhaustively methylated-treated with a methylating agent (methyl iodide) that replaces the hydrogen of every sugar hydroxyl with a methyl group, converting –OH to –OCH3. All the glycosidic bonds in the treated sample are then hydrolyzed in aqueous acid, and the amounts of α -D-2,3-di-O-methylglucopyranose and α -D-2,3,6-tri-O-methylglucopyranose formed are measured. 1- Draw the cyclic structure of α-D-glucopyranose, α-D-2,3-di-O-methylglucopyranose and α-D-2,3,6-tri-O-methylglucopyranose, including the numbering of carbon atoms. 2- Which of α-D-2,3-di-O-methylglucopyranose or α-D-2,3,6-tri-O-methylglucopyranose represents a glucose unit in glycogen which was originally carrying a α 1⟶ 6 glycosidic bond? Explain.

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5-Bromouracil, a highly mutagenic compound (that is, a compound that causes changes in DNA), is used in cancer chemotherapy. When administeredto a patient, it is converted to the triphosphate and incorporated into DNA in place of thymine, which it resembles sterically. Why does it causemutations?(Hint: The bromo substituent increases the stability of the enol tautomer.)