Synthesis of sequential polydepsipeptides utilizing a new approach for the synthesis of depsipeptides.
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.
Katakai
Ryoichi
R
Department of Chemistry, Gunma University, Tenjin-cho, Kiryu 376-8515, Japan. katakai@chem.gunma-u.ac.jp
Kobayashi
Kyoko
K
Yamada
Keiichi
K
Oku
Hiroyuki
H
Emori
Nobu
N
D015761:4-Aminopyridine / Q000031:analogs & derivatives* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001704:Biopolymers / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D006880:Hydroxy Acids / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry
D000596:Amino Acids; D001704:Biopolymers; D004952:Esters; D006880:Hydroxy Acids; D009842:Oligopeptides; D013388:Succinimides; D015761:4-Aminopyridine; C001426:N-hydroxysuccinimide; C003885:4-dimethylaminopyridine