Synthesis of fluorinated chitin derivatives via enzymatic polymerization.
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]
Makino
Akira
A
Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
Ohmae
Masashi
M
Kobayashi
Shiro
S
D002384:Catalysis; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002688:Chitinases / Q000737:chemistry / Q000378:metabolism*; D015195:Drug Design; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011108:Polymers / Q000737:chemistry; D013329:Structure-Activity Relationship
D017611:Fluorine Compounds; D011108:Polymers; D002686:Chitin; D002688:Chitinases