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Synthesis of Fluorinated Chitin Derivatives via Enzymatic Polymerization
Author(s) -
Makino Akira,
Ohmae Masashi,
Kobayashi Shiro
Publication year - 2006
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.200600128
Subject(s) - chitin , chitobiose , monomer , chitinase , chemistry , polymerization , regioselectivity , polysaccharide , polymer chemistry , chitosan , derivative (finance) , enzyme catalysis , organic chemistry , catalysis , enzyme , polymer , financial economics , economics
Summary: Synthesis of fluorinated chitin derivatives has been achieved using chitinase from Bacillus sp. as a catalyst. 6′‐Fluoro‐ ( 1a ), 6‐fluoro‐ ( 1b ) and 6,6′‐difluoro‐ ( 1c ) chitobiose oxazoline derivatives were newly prepared as TSAS monomers for chitinase. Ring‐opening polyaddition of these monomers proceeded effectively at pH 8.0–9.0 and 30–40 °C, giving rise to alternatingly 6‐fluorinated chitin derivatives ( 2a and 2b ) from 1a and 1b , and fully 6‐fluorinated chitin derivative ( 2c ) from 1c under total control of regioselectivity and stereochemistry. XRD measurements revealed that polysaccharides 2a and 2b had crystalline structures similar to that of α ‐chitin.