Synthesis of the protected 6-16 segment of zervamicin 11-2, an application of the azirine/oxazolone method.
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-2H-azirin-3-amine was used as the building block for Aib(7), methyl 2,2-dimethyl-2H-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 2H-azirin-3-amines were performed in 75% to quantitative yield.
Pradeille
Nicolas
N
Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland.
Heimgartner
Heinz
H
D000621:Aminoisobutyric Acids; D001389:Azirines; D005656:Fungal Proteins / Q000138:chemical synthesis*; D010081:Oxazolone; D054848:Peptaibols; D010446:Peptide Fragments / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*
D000621:Aminoisobutyric Acids; D001389:Azirines; D005656:Fungal Proteins; D054848:Peptaibols; D010446:Peptide Fragments; D010455:Peptides; D010081:Oxazolone; C077077:zervamicin IIB