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Synthesis of the protected 6–16 segment of zervamicin II-2, an application of the azirine/oxazolone method

✍ Scribed by Nicolas Pradeille; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
158 KB
Volume
9
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

The protected 11 amino acid segment (6–16) of the peptaibol zervamicin II‐2 was synthesized by using the ‘azirine/oxazolone method’ for the introduction of all Aib residues. Whereas a 2,2‐dimethyl‐2__H__‐azirin‐3‐amine was used as the building block for Aib(7), methyl 2,2‐dimethyl‐2__H__‐azirine‐3‐prolinate and ‐3‐(3‐hydroxyprolinate) proved to be ideally suited as dipeptide synthons for the introduction of Aib‐Pro and Aib‐Hyp, respectively. The coupling of Z‐protected amino acids or peptide acids with the 2__H__‐azirin‐3‐amines were performed in 75% to quantitative yield. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.

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