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

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

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
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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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, 2012, p. 689-690.

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

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.",

author = "Naoki Yoshida and Tomonari Tanaka and Masato Noguchi and Atsushi Kobayashi and Kumiko Ishikura and Tatsuya Ikenuma and Hiromu Seno and Takeshi Watanabe and Michinari Kohri and Shoda, {Shin Ichiro}",

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AU - Tanaka, Tomonari

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AU - Kobayashi, Atsushi

AU - Ishikura, Kumiko

AU - Ikenuma, Tatsuya

AU - Seno, Hiromu

AU - Watanabe, Takeshi

AU - Kohri, Michinari

AU - Shoda, Shin Ichiro

PY - 2012

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

Abstract

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