Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition sttate analogue substrate

Shin Ichiro Shoda; Yoshinori Misawa; Yousuke Nishijima; Yukiko Tawata; Tomohiko Kotake; Masato Noguchi; Atsushi Kobayashi; Takeshi Watanabe

doi:10.1007/s10570-006-9066-z

Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition sttate analogue substrate

Shin Ichiro Shoda, Yoshinori Misawa, Yousuke Nishijima, Yukiko Tawata, Tomohiko Kotake, Masato Noguchi, Atsushi Kobayashi, Takeshi Watanabe

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapi d hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)-β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase.

Original language	English
Pages (from-to)	477-484
Number of pages	8
Journal	Cellulose
Volume	13
Issue number	4
DOIs	https://doi.org/10.1007/s10570-006-9066-z
Publication status	Published - 2006 Aug
Externally published	Yes

Keywords

1,2-Oxazoline derivative
Chitinase
Enzymatic polyaddition
N-acetyllactosamine
Oligo-N-acetyllactosaminoglycan

ASJC Scopus subject areas

Polymers and Plastics

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10.1007/s10570-006-9066-z

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@article{4756aa7e7db5447cbea7b9de23b9ca5b,

title = "Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition sttate analogue substrate",

abstract = "Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapi d hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)-β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase.",

keywords = "1,2-Oxazoline derivative, Chitinase, Enzymatic polyaddition, N-acetyllactosamine, Oligo-N-acetyllactosaminoglycan",

author = "Shoda, {Shin Ichiro} and Yoshinori Misawa and Yousuke Nishijima and Yukiko Tawata and Tomohiko Kotake and Masato Noguchi and Atsushi Kobayashi and Takeshi Watanabe",

note = "Funding Information: S. S. gratefully acknowledges financial support from the Ministry of Education, Culture, Sports, Science and Technology, Japan for a Grant-in Aid for Scientific Research (No. 17350053). We thank Yaizu Suisankagaku Industry for providing us with N-acetyllactosamine.",

year = "2006",

month = aug,

doi = "10.1007/s10570-006-9066-z",

language = "English",

volume = "13",

pages = "477--484",

journal = "Cellulose",

issn = "0969-0239",

publisher = "Springer Netherlands",

number = "4",

}

TY - JOUR

T1 - Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition sttate analogue substrate

AU - Shoda, Shin Ichiro

AU - Misawa, Yoshinori

AU - Nishijima, Yousuke

AU - Tawata, Yukiko

AU - Kotake, Tomohiko

AU - Noguchi, Masato

AU - Kobayashi, Atsushi

AU - Watanabe, Takeshi

N1 - Funding Information: S. S. gratefully acknowledges financial support from the Ministry of Education, Culture, Sports, Science and Technology, Japan for a Grant-in Aid for Scientific Research (No. 17350053). We thank Yaizu Suisankagaku Industry for providing us with N-acetyllactosamine.

PY - 2006/8

Y1 - 2006/8

N2 - Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapi d hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)-β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase.

AB - Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapi d hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)-β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase.

KW - 1,2-Oxazoline derivative

KW - Chitinase

KW - Enzymatic polyaddition

KW - N-acetyllactosamine

KW - Oligo-N-acetyllactosaminoglycan

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ER -

Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition sttate analogue substrate

Abstract

Keywords

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