Synthesis of fluorinated chitin derivatives via enzymatic polymerization

Macromol Biosci. 2006 Oct 20;6(10):862-72. doi: 10.1002/mabi.200600128.

Abstract

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 degrees 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 alpha-chitin. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chitin / analogs & derivatives*
  • Chitin / chemical synthesis*
  • Chitin / chemistry
  • Chitinases / chemistry
  • Chitinases / metabolism*
  • Drug Design
  • Fluorine Compounds / chemical synthesis*
  • Fluorine Compounds / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Polymers / chemistry
  • Structure-Activity Relationship

Substances

  • Fluorine Compounds
  • Polymers
  • Chitin
  • Chitinases