Bucher, Christoph, Linden, Anthony and Heimgartner, Heinz (2020) Synthesis and Solid State Conformation of Tetrapeptide Amides Containing two Aib and two (Me)Phe Residues – Use of Enantiomerically Pure 2-Benzyl-2-methyl-2H-azirin-3-amines as (Me)Phe-Synthons. Chemistry & Biodiversity. ISSN 1612-18721612-1880

Abstract

A series of tetrapeptide amides containing two aminoisobutyric acids (Aib) and two -methylphenylalanine ((Me)Phe) units were prepared via the ‘azirine/oxazolone method’. New 2-benzyl-2-methyl-2H-azirine-3-amines have been used for the selective introduction of (S)- and (R)-(Me)Phe, respectively. The solid-state conformations of five tetrapeptide amides were determined by X-ray crystallography. In all cases, two -turns stabilize 310-helical conformations and it was confirmed that, in contrast to proteinogenic amino acids, the configuration of (Me)Phe does not determine the screw-sense of the helix.

Item Type:	Article
Keywords:	2H-azirin-3-amines • X-ray crystallography, methylphenylalanine, azirine/oxazolone method, peptide conformation
Date Deposited:	26 May 2020 00:45
Last Modified:	26 May 2020 00:45
URI:	https://oak.novartis.com/id/eprint/42727