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Synthesis of Z‐Protected Aib‐ and Phe(2Me)‐Containing Pentapeptides and Their Crystal Structures
Author(s) -
Arnhold Franziska S.,
Linden Anthony,
Heimgartner Heinz
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400084
Subject(s) - chemistry , pentapeptide repeat , oxazolone , stereochemistry , crystal structure , azirine , crystallography , amino acid , ring (chemistry) , peptide , organic chemistry , biochemistry
A series of pentapeptide derivatives containing α , α ‐disubstituted α ‐amino acids have been prepared by a combination of the ‘azirine/oxazolone method’ and segment condensations. X‐Ray crystal‐structure determinations of the molecular structures confirmed the presence of helical conformations stabilized by β ‐turns of type III or III′. Pentapeptides containing ( R )‐Phe(2Me) form a right‐handed helix, whereas those containing ( S )‐Phe(2Me) adopt a left‐handed helical structure.
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