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Synthesis of Peptides Containing α,α‐Disubstituted α‐Amino Acids by the Azirine/Oxazolone Method: The (12–20)‐Nonapeptide of the Ionophore Alamethicin
Author(s) -
Wipf Peter,
Heimgartner Heinz
Publication year - 1990
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.19900730103
Subject(s) - chemistry , alamethicin , oxazolone , aminoisobutyric acid , azirine , synthon , ionophore , stereochemistry , amino acid , organic chemistry , biochemistry , membrane , ring (chemistry) , lipid bilayer
The (12–20)‐nonapeptide Z‐Leu‐Aib‐Pro‐Val‐Aib‐Aib‐Glu (OBzl)‐Gln‐Pheol ( 10 ) of the ionophor alamethicin was synthesized by a new strategy, using 3‐amino‐2,2‐dimethyl‐2 H ‐azirines 2 as synthons for the α‐aminoisobutyric acid (Aib) moieties.