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Synthesis and Solid State Conformation of Tetrapeptide Amides Containing two Aib and two (αMe)Phe Residues – Use of Enantiomerically Pure 2-Benzyl-2-methyl-2H-azirin-3-amines as (αMe)Phe-Synthons


Bucher, Christoph B; Linden, Anthony; Heimgartner, Heinz (2020). Synthesis and Solid State Conformation of Tetrapeptide Amides Containing two Aib and two (αMe)Phe Residues – Use of Enantiomerically Pure 2-Benzyl-2-methyl-2H-azirin-3-amines as (αMe)Phe-Synthons. Chemistry & Biodiversity, 17(7):e2000246.

Abstract

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

Abstract

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

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1 July 2020
Deposited On:19 Jun 2020 05:45
Last Modified:05 May 2021 00:00
Publisher:Wiley-VCH Verlag
ISSN:1612-1872
OA Status:Green
Publisher DOI:https://doi.org/10.1002/cbdv.202000246
Project Information:
  • : FunderSNF
  • : Grant ID
  • : Project Title
  • : FunderF. Hoffmann-La Roche AG, Basel
  • : Grant ID
  • : Project Title

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