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.
2H-azirin-3-amines
X-ray crystallography
amino acids
azirine/oxazolone method
conformation analysis
peptide conformation
α-methylphenylalanine
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Jul 2020
Jul 2020
Historique:
received:
31
03
2020
accepted:
05
05
2020
pubmed:
6
5
2020
medline:
26
5
2021
entrez:
6
5
2020
Statut:
ppublish
Résumé
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 3
Identifiants
pubmed: 32368841
doi: 10.1002/cbdv.202000246
doi:
Substances chimiques
Amides
0
Aminoisobutyric Acids
0
Oligopeptides
0
alpha-methylphenylalanine
4415-69-4
Phenylalanine
47E5O17Y3R
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000246Subventions
Organisme : Swiss National Science Foundation
Pays : Switzerland
Informations de copyright
© 2020 Wiley-VHCA AG, Zurich, Switzerland.
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