Enzymatic Polymerization to Novel Polysaccharides Having a Glucose-N-acetylglucosamine Repeating Unit, a Cellulose-Chitin Hybrid Polysaccharide
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- 作者：Shiro Kobayashi ; Akira Makino ; Hironori Matsumoto ; Shigeru Kunii ; Masashi Ohmae ; Toshitsugu Kiyosada ; Ken Makiguchi ; Akira Matsumoto ; Michinobu Horie ; and Shin-Ichiro Shoda
- 刊名：Biomacromolecules
- 出版年：2006
- 出版时间：May 2006
- 年：2006
- 卷：7
- 期：5
- 页码：1644 - 1656
- 全文大小：639K
- 年卷期：v.7,no.5(May 2006)
- ISSN：1526-4602
文摘
A cellulose-chitin hybrid polysaccharide having alternatingly 
(1
4)-linked D-glucose (Glc) and N-acetyl-D-glucosamine (GlcNAc) was synthesized via two modes of enzymatic polymerization. First, a sugar oxazolinemonomer of Glc(14)GlcNAc (1) was designed as a transition-state analogue substrate (TSAS) monomer forchitinase catalysis. Monomer 1 was recognized by chitinase from Bacillus sp., giving rise to a cellulose-chitinhybrid polysaccharide (2) via ring-opening polyaddition with perfect regioselectivity and stereochemistry. Molecularweight (Mn) of 2 reached 4030, which corresponds to 22 saccharide units. Second, a sugar fluoride monomer ofGlcNAc(14)Glc (3) was synthesized for the catalysis of cellulase from Trichoderma viride. The enzymecatalyzed polycondensation of 3, providing a cellulose-chitin hybrid polysaccharide (4) in regio- and stereoselectivemanner. Mn of 4 reached 2840, which corresponds to 16 saccharide units. X-ray diffraction measurements revealedthat these hybrid polysaccharides did not form any characteristic crystalline structures. Furthermore, these unnaturalhybrids of 2 and 4 were successfully digested by lysozyme from human neutrophils.
(14)-linked D-glucose (Glc) and N-acetyl-D-glucosamine (GlcNAc) was synthesized via two modes of enzymatic polymerization. First, a sugar oxazolinemonomer of Glc(14)GlcNAc (1) was designed as a transition-state analogue substrate (TSAS) monomer forchitinase catalysis. Monomer 1 was recognized by chitinase from Bacillus sp., giving rise to a cellulose-chitinhybrid polysaccharide (2) via ring-opening polyaddition with perfect regioselectivity and stereochemistry. Molecularweight (Mn) of 2 reached 4030, which corresponds to 22 saccharide units. Second, a sugar fluoride monomer ofGlcNAc(14)Glc (3) was synthesized for the catalysis of cellulase from Trichoderma viride. The enzymecatalyzed polycondensation of 3, providing a cellulose-chitin hybrid polysaccharide (4) in regio- and stereoselectivemanner. Mn of 4 reached 2840, which corresponds to 16 saccharide units. X-ray diffraction measurements revealedthat these hybrid polysaccharides did not form any characteristic crystalline structures. Furthermore, these unnaturalhybrids of 2 and 4 were successfully digested by lysozyme from human neutrophils.