Chemoenzymatic Synthesis of Fucose- or Rhamnose-Branched Polymer

• Published in: Macromolecular bioscience Vol. 3; no. 3-4; pp. 151 - 156
• Main Authors: Raku, Takao, Tokiwa, Yutaka
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.04.2003; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: 6-deoxy sugar; Applied sciences; Bacillus subtilis; biodegradable; enzymes; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; Polymerization; polysaccharides; Preparation, kinetics, thermodynamics, mechanism and catalysts; Pseudomonas; radical polymerization; Streptomyces griseus; Enzymatic synthesis; Aldose; Regioselectivity; Enzyme; Triacylglycerol lipase; Esterases; Experimental study; Esterification; Lateral group; Carboxylic ester hydrolases; Peptidases; Free radical polymerization; Preparation; Hydrolases; Monomer; Vinyl ester polymer
• ISSN: 1616-5187; 1616-5195
• DOI: 10.1002/mabi.200390019

6‐Deoxy sugars having only secondary alcohols, namely, D‐fucose, L‐fucose, and L‐rhamnose, were regioselectively esterified with divinyl adipate by enzymes. The compounds 2‐O‐vinyl adipolyl D‐fucose and 2‐O‐vinyl adipolyl L‐fucose were effectively produced in dimethylformamide by protease from Bacillus subtilis and Streptomyces griseus. Furthermore, 4‐O‐vinyl adipolyl L‐rhamnose was effectively produced in pyridine by lipase from Pseudomonas sp. Each polymerizable sugar ester was polymerized by 1,1′‐azoisobutyronitrile to give polymers having a number average molecular weight of 5 000–14 000. Part of the chemoenzymatic synthesis of poly(6‐deoxy sugars).