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Novel N ‐(2,2‐Dimethyl‐2 H ‐azirin‐3‐yl)‐ L ‐prolinates as Aib‐Pro Synthons
Author(s) -
Stamm Simon,
Heimgartner Heinz
Publication year - 2006
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.200690178
Subject(s) - chemistry , synthon , oxazolone , azirine , amine gas treating , peptide , phenacyl , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , ring (chemistry)
The syntheses of phenacyl N ‐(2,2‐dimethyl‐2 H ‐azirin‐3‐yl)‐ L ‐prolinate and allyl N ‐(2,2‐dimethyl‐2 H ‐azirin‐3‐yl)‐ L ‐prolinate are reported. Reactions of these 2 H ‐azirin‐3‐amine derivatives with Z‐protected amino acids have shown them to be suitable synthons for the Aib‐Pro unit in peptide synthesis. After incorporation into the peptide by means of the ‘azirine/oxazolone method’, the C‐termini of the resulting peptides were deprotected selectively with Zn in AcOH or by a mild Pd 0 ‐promoted procedure, respectively.
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