Chapter 26, Problem 42P

Interpretation Introduction

Interpretation:

The protected amino acid that should be anchored to the solid support in the first step of a synthesis of oxytocin by the Merrifield method is to be determined.

Concept Introduction:

Merrifield method of peptide synthesis is carried out on a solid polymer surface, with $-{\text{CH}}_{\text{2}}\text{Cl}$ groups on its surface.

The synthesis starts with anchoring the C terminus of the peptide chain to the polymer via nucleophilic substitution of chlorine in the $-{\text{CH}}_{\text{2}}\text{Cl}$ group on the polymer surface.

The peptide chain is assembled by successive reaction between the amino group of the anchored amino acid/chain with the carboxyl group of the next $\text{N-protected}$ amino acid.