Combinatorial solid-phase synthesis of hapalosin mimetics.
The solid-phase synthesis of a small library of mimetics of the cyclic depsipeptide hapalosin is described. 3-Amino-4-hydroxy-5-nitrobenzoic acid was anchored through the anilino moiety to a backbone amide linker (BAL) handle support. Using chemoselective reactions and without the need for protecting group manipulations, the benzoic acid group was first amidated, then the aniline nitrogen was acylated, and finally the nitro group was reduced to an amine and acylated or reductively alkylated, to generate a 12-member library.
Olsen
J A
JA
Department of Organic Chemistry, Kemitorvet, Technical University of Denmark, Lyngby.
Jensen
K J
KJ
Nielsen
J
J
D000478:Alkylation; D000814:Aniline Compounds / Q000737:chemistry; D002625:Chemistry, Organic; D047630:Depsipeptides; D007202:Indicators and Reagents; D007769:Lactams / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D008956:Models, Chemical; D055601:Organic Chemistry Phenomena; D019151:Peptide Library
D000814:Aniline Compounds; D047630:Depsipeptides; D007202:Indicators and Reagents; D007769:Lactams; D007783:Lactones; D019151:Peptide Library; C111358:hapalosin