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Solid‐Phase Synthesis of Aza‐Kahalalide F Analogues: (2 R ,3 R )‐2‐Amino‐3‐azidobutanoic Acid as Precursor of the Aza‐Threonine
Author(s) -
Izzo Irene,
Acosta Gerardo A.,
TullaPuche Judit,
Cupido Tommaso,
MartinLopez Maria Jesus,
Cuevas Carmen,
Albericio Fernando
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901345
Subject(s) - chemistry , solid phase synthesis , threonine , azide , stereochemistry , amino acid , peptide synthesis , combinatorial chemistry , organic chemistry , peptide , serine , biochemistry , enzyme
The solid‐phase synthesis of six novel analogues of Kahalalide F (KF), a natural product currently undergoing Phase II clinical trials, is reported. In all these compounds, amides were used as isosteres for the depsi bond. For two of these compounds, we performed an efficient synthesis of N ‐Fmoc‐protected (2 R ,3 R )‐2‐amino‐3‐azidobutanoic acid, precursor of the aza‐threonine. This is the first example of the solid‐phase reduction of an azide group in the preparation of aza‐Thr‐containing peptides in the solid phase.