Lehninger Principles of Biochemistry 7E & SaplingPlus for Lehninger Principles of Biochemistry 7E (Six-Month Access)
Lehninger Principles of Biochemistry 7E & SaplingPlus for Lehninger Principles of Biochemistry 7E (Six-Month Access)
7th Edition
ISBN: 9781319125882
Author: David L. Nelson, Michael M. Cox
Publisher: W. H. Freeman
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Chapter 3, Problem 1P
Summary Introduction

To determine: Whether the given Citrulline structure is L-amino acid or D-amino acid.

Introduction: Isomers are the compounds that have similar molecular formula, but different structural formula. L-form (levorotatory) and D-form (dextrorotatory) are optical isomers or stereoisomers. They have the same chemical structure, but their spatial arrangement is different.

Expert Solution & Answer
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Answer to Problem 1P

Correct answer: The given structure of Citrulline is in L-conformation.

Explanation of Solution

Explanation:

In D-Citrulline, the amino group (-NH2) present on the penultimate carbon is on the right side. In L-Citrulline, the amino group (-NH2) present on the penultimate carbon is on the left side. In the given case, the amino group is present on the left side and thus, the given structure is L-conformation of Citrulline.

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The beta-lactamase hydrolyzes the lactam-ring in penicillin. Describe the mechanism  of hydrolysis, insuring to include the involvement of S, D, & K in the reaction sequence. Please help
To map the active site of beta-lactamase, the enzyme was hydrolyzed with trypsin to yield a hexapeptide (P1) with the following amino acids. Glu, Lys, Leu, Phe, Met, and Ser. Treatment of P1 with phenyl isothiocyanate yielded a PTH derivative of phenylalanine and a peptide (P2). Treatment of P1 with cyanogenbromide gave an acidic tetrapeptide (P3) and a dipeptide (P4).Treatment of P2 with 1-fluoro-2,4-dinitrobenzene, followed by complete hydrolysis, yields N-2,4-dinitrophenyl-Glu. P1, P2, and P3 contain the active site serine. Why doesn't D in this hexapeptide not participate in the hydrolysis of the beta-lactam ring even though S, K, and D are involved in the catalyst?
To map the active site of -lactamase, the enzyme was hydrolyzed with trypsin to yield a hexapeptide (P1) with the following amino acids. Glu, Lys, Leu, Phe, Met, and Ser. Treatment of P1 with phenyl isothiocyanate yielded a PTH derivative of phenylalanine and a peptide (P2). Treatment of P1 with cyanogenbromide gave an acidic tetrapeptide (P3) and a dipeptide (P4).Treatment of P2 with 1-fluoro-2,4-dinitrobenzene, followed by complete hydrolysis, yields N-2,4-dinitrophenyl-Glu. P1, P2, and P3 contain the active site serine.  Using the experimental results described above derive the primary sequence of the active site hexapeptide. Please help!
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