Synthesis of Cell-Recognizable Sugar-Peptide Conjugates by Living Ring-Opening Polymerization

通过开环聚合合成细胞可识别的糖肽缀合物

基本信息

批准号：
07651081
负责人：
OKADA Masahiko
金额：
$ 1.41万
依托单位：
Nagoya University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1996
项目状态：
已结题

项目摘要

Well-defined glycopeptide-containing block copolymers were synthesized by ring-opening polymerization of a sugar-substituted alpha-amino acid N-carboxyanhydride (NCA), i.e., O-(tetra-O-acetyl-beta-D-gluco-pyranosyl)-L-serine NCA (1), initiated with omega-amine-terminated poly (2-methyl-2-oxazoline) and poly (2-phenyl-2-oxazoline) macroinitiators in dichloromethane at 27ﾟC.DPs of peptide segments of the resulting poly (2-methyl-2-oxazoline)-block-poly [O-(tetra-O-acetyl-beta-D-glucopyranosyl)-L-serine](2a) and poly (2-phenyl-2-oxazoline)-block-poly [O-(tetra-O-acetyl-beta-D-glucopyranosyl)-L-serine](2b) were close to monomer/macroinitiator feed molar ratios. Glycopeptide-bearing block copolymers, poly (2-methyl-2-oxazoline)-block-poly [O-(beta-D-glucopyranosyl)-L-serine] and poly (2-phenyl-2-oxazoline)-block-poly [O-(beta-D-glucopyranosyl)-L-serine], were derived from 2a and 2b, respectively, by deacetylation with hydrazine monohydrate.First synthesis of well-defined glycopeptide macromonomers with an alpha-styryl group was performed by living ring-opening polymerization of sugar-substituted NCAs, i.e., 1 and O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-L-serine NCA,followed by deacetylation with hydrazine monohydrate in methanol at 0ﾟC.Water-soluble copolymer between the macromonomer and acrylamide was obtained by the radical copolymerization with 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPD) as an initiator in water at 55ﾟC.

通过糖取代的α-氨基氨基酸N-羧基氢化物（NCA）（即o- o-（tetra-o-o-o-acetyyl-beta-d---甘酸 - 葡萄糖） - lucuco-pyranosyl-l-l-ser-enmine nca（1），起始起始OME OME OME OME OMEINGIN-OMEINGIN-OMEINGIAN-1） (2-methyl-2-oxazoline) and poly (2-phenyl-2-oxazoline) macroinitiators in dichloromethane at 27ﾟC.DPs of pepper segments of the resulting poly (2-methyl-2-oxazoline)-block-poly [O-(tetra-O-acetyl-beta-D-glucopyranosyl)-L-serine](2a) and poly （2-苯基-2-恶唑啉） - 块状 - 聚[O-（TETRA-O-乙酰-Beta-D-丙糖基）-l-甲氨酸]（2B）（2B）接近单体/大型引起剂摩尔比。 Glycopeptide-bearing block copolymers, poly (2-methyl-2-oxazoline)-block-poly [O-(beta-D-glucopyranosyl)-L-serine] and poly (2-phenyl-2-oxazoline)-block-poly [O-(beta-D-glucopyranosyl)-L-serine], were derived from 2a and 2b, respectively, by deacetylation with氢氮单水合物。首先合成明确定义的糖肽宏观工具与α-式晶体组是通过糖取代的NCAS的生存环的聚合进行的，即1，即1，即1和1 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-L-serine NCA,followed by deacetylation with hydrozine monohydrate in methanol at 0ﾟC.Water-soluble copolymer between the macromonomer and acrylicamide was obtained by the radical copolymerization with 2,2'-azobis（2-氨基苯丙胺）二氢氯化物（AAPD）作为55 C. C.