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Synthesis of sequential polydepsipeptides utilizing a new approach for the synthesis of depsipeptides
Author(s) -
Katakai Ryoichi,
Kobayashi Kyoko,
Yamada Keiichi,
Oku Hiroyuki,
Emori Nobu
Publication year - 2004
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20013
Subject(s) - depsipeptide , chemistry , tetrahydrofuran , acetonitrile , amino acid , hydrogenolysis , organic chemistry , combinatorial chemistry , solvent , catalysis , stereochemistry , biochemistry
Sequential polydepsipeptides were synthesized by the depsipeptide active ester method using a new approach for the direct synthesis of N‐protected depsipeptide free acids from hydroxy acids. The method uses synthesis of Boc‐didepsipeptides by reaction of free hydroxy acids with Boc‐amino acid N ‐hydroxysuccinimide esters catalyzed by 4‐dimethylaminopyridine and chain elongation of the free depsipeptides by the reaction with Boc‐amino acid N ‐hydroxysuccinimide esters in an organic solvent system of acetonitrile‐tetrahydrofuran. The Boc‐depsipeptide free acids were activated as their N ‐hydroxysuccinimide esters, which were polymerized after removal of the Boc‐protecting group. © 2004 Wiley Periodicals, Inc. Biopolymers, 2004