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Synthesis of Fluorinated Chitin Derivatives via Enzymatic Polymerization

✍ Scribed by Akira Makino; Masashi Ohmae; Shiro Kobayashi

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 262 KB
Volume: 6
Category: Article
ISSN: 1616-5187
DOI: 10.1002/mabi.200600128

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✦ Synopsis

Abstract

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.
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