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Synthesis of the protected 6–16 segment of zervamicin II‐2, an application of the azirine/oxazolone method
Author(s) -
Pradeille Nicolas,
Heimgartner Heinz
Publication year - 2003
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.522
Subject(s) - azirine , oxazolone , dipeptide , synthon , chemistry , amino acid , yield (engineering) , amine gas treating , stereochemistry , biochemistry , organic chemistry , materials science , ring (chemistry) , metallurgy
The protected 11 amino acid segment (6–16) of the peptaibol zervamicin II‐2 was synthesized by using the ‘azirine/oxazolone method’ for the introduction of all Aib residues. Whereas a 2,2‐dimethyl‐2 H ‐azirin‐3‐amine was used as the building block for Aib(7), methyl 2,2‐dimethyl‐2 H ‐azirine‐3‐prolinate and ‐3‐(3‐hydroxyprolinate) proved to be ideally suited as dipeptide synthons for the introduction of Aib‐Pro and Aib‐Hyp, respectively. The coupling of Z‐protected amino acids or peptide acids with the 2 H ‐azirin‐3‐amines were performed in 75% to quantitative yield. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.