An activated O→ N acyl transfer auxiliary: efficient amide-backbone substitution of hindered “difficult” peptides

LP Miranda, WDF Meutermans…

Index: Miranda; Meutermans; Smythe; Alewood The Journal of organic chemistry, 2000 , vol. 65, # 18 p. 5460 - 5468

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Citation Number: 61

Abstract

Overcoming the phenomenon known as “difficult” synthetic sequences has been a major goal in solid-phase peptide synthesis for over 30 years. In this work the advantages of amide backbone-substitution in the solid-phase synthesis of “difficult” peptides are augmented by developing an activated N α-acyl transfer auxiliary. Apart from disrupting troublesome intermolecular hydrogen-bonding networks, the primary function of the activated N α- ...