Chapter 26.5, Problem 10P

Interpretation Introduction

Interpretation:

In peptide analysis, -SH groups of cysteine are capped by S_N2 reaction with iodoacetate.

Concept introduction:

In preparation for analysis, the peptide is broken into its constituent amino acids by reducing all disulfide bonds, capping the -SH groups of cysteine residues by S_N2 reaction with iodoacetic acid, and hydrolyzing the amide bonds by heating with aqueous 6 M HCl at 110°C for 24 hours.

To determine:

Structure of product that would be obtained by S_N2 reaction of cysteine and iodoacetic acid.