One-pot chemoenzymatic route to chitoheptaose via specific transglycosylation of chitopentaoseoxazoline on chitinase-template

Naoki Yoshida; Tomonari Tanaka; Masato Noguchi; Atsushi Kobayashi; Kumiko Ishikura; Tatsuya Ikenuma; Hiromu Seno; Takeshi Watanabe; Michinari Kohri; Shin Ichiro Shoda

doi:10.1246/cl.2012.689

One-pot chemoenzymatic route to chitoheptaose via specific transglycosylation of chitopentaoseoxazoline on chitinase-template

Naoki Yoshida, Tomonari Tanaka, Masato Noguchi, Atsushi Kobayashi, Kumiko Ishikura, Tatsuya Ikenuma, Hiromu Seno, Takeshi Watanabe, Michinari Kohri, Shin Ichiro Shoda

ENG - Biomolecular Engineering

Research output: Contribution to journal › Article

14 Citations (Scopus)

Abstract

One-pot regio- and stereospecific synthesis of chitoheptaose ((GlcNAc) ₇) has been achieved by using chitopentaose ((GlcNAc) ₅) and chitobiose ((GlcNAc) ₂) as starting materials. The key intermediate, 1,2-oxazoline derivative of (GlcNAc) ₅, could be directly prepared in water and successfully transglycosylated to (GlcNAc) ₂ catalyzed by a mutant chitinase with lower hydrolyzing activity.

Original language	English
Pages (from-to)	689-690
Number of pages	2
Journal	Chemistry Letters
Volume	41
Issue number	7
DOIs	https://doi.org/10.1246/cl.2012.689
Publication status	Published - 2012 Jul 30

ASJC Scopus subject areas

Chemistry(all)

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Yoshida, N., Tanaka, T., Noguchi, M., Kobayashi, A., Ishikura, K., Ikenuma, T., Seno, H., Watanabe, T., Kohri, M., & Shoda, S. I. (2012). One-pot chemoenzymatic route to chitoheptaose via specific transglycosylation of chitopentaoseoxazoline on chitinase-template. Chemistry Letters, 41(7), 689-690. https://doi.org/10.1246/cl.2012.689

One-pot chemoenzymatic route to chitoheptaose via specific transglycosylation of chitopentaoseoxazoline on chitinase-template. / Yoshida, Naoki; Tanaka, Tomonari; Noguchi, Masato; Kobayashi, Atsushi; Ishikura, Kumiko; Ikenuma, Tatsuya; Seno, Hiromu; Watanabe, Takeshi; Kohri, Michinari; Shoda, Shin Ichiro.

In: Chemistry Letters, Vol. 41, No. 7, 30.07.2012, p. 689-690.

Research output: Contribution to journal › Article

Yoshida, Naoki ; Tanaka, Tomonari ; Noguchi, Masato ; Kobayashi, Atsushi ; Ishikura, Kumiko ; Ikenuma, Tatsuya ; Seno, Hiromu ; Watanabe, Takeshi ; Kohri, Michinari ; Shoda, Shin Ichiro. / One-pot chemoenzymatic route to chitoheptaose via specific transglycosylation of chitopentaoseoxazoline on chitinase-template. In: Chemistry Letters. 2012 ; Vol. 41, No. 7. pp. 689-690.

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abstract = "One-pot regio- and stereospecific synthesis of chitoheptaose ((GlcNAc) 7) has been achieved by using chitopentaose ((GlcNAc) 5) and chitobiose ((GlcNAc) 2) as starting materials. The key intermediate, 1,2-oxazoline derivative of (GlcNAc) 5, could be directly prepared in water and successfully transglycosylated to (GlcNAc) 2 catalyzed by a mutant chitinase with lower hydrolyzing activity.",

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