An expeditious route to GlcNAc-Cbz-Asn by chemo-enzymatic synthesis

Y. Tokuda; Y. Takahashi; K. Matoishi; Y. Ito; T. Sugai

doi:10.1055/s-2002-19355

An expeditious route to GlcNAc-Cbz-Asn by chemo-enzymatic synthesis

Y. Tokuda, Y. Takahashi, K. Matoishi, Y. Ito, T. Sugai

School of Pharmaceutical Sciences

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

4 Citations (Scopus)

Abstract

A short-step route to GlcNAc-Cbz-Asn was developed. Treatment of GlcNAc in sat. aq. NH₄HCO₃ solution and subsequent electorodialytic desalting provided ammonia-free glycosylamine in large quantity. The product was coupled with Cbz-Asn α-isobutyl ester β-fluoride, and finally, the isobutyl ester was deprotected by enzyme-catalyzed hydrolysis under mild conditions.

Original language	English
Pages (from-to)	57-60
Number of pages	4
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2002-19355
Publication status	Published - 2002 Jan 1

Keywords

Amino acids
Coupling
Enzymes
Glycosides
Hydrolyses

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2002-19355

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abstract = "A short-step route to GlcNAc-Cbz-Asn was developed. Treatment of GlcNAc in sat. aq. NH4HCO3 solution and subsequent electorodialytic desalting provided ammonia-free glycosylamine in large quantity. The product was coupled with Cbz-Asn α-isobutyl ester β-fluoride, and finally, the isobutyl ester was deprotected by enzyme-catalyzed hydrolysis under mild conditions.",

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author = "Y. Tokuda and Y. Takahashi and K. Matoishi and Y. Ito and T. Sugai",

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AU - Tokuda, Y.

AU - Takahashi, Y.

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AU - Ito, Y.

AU - Sugai, T.

PY - 2002/1/1

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N2 - A short-step route to GlcNAc-Cbz-Asn was developed. Treatment of GlcNAc in sat. aq. NH4HCO3 solution and subsequent electorodialytic desalting provided ammonia-free glycosylamine in large quantity. The product was coupled with Cbz-Asn α-isobutyl ester β-fluoride, and finally, the isobutyl ester was deprotected by enzyme-catalyzed hydrolysis under mild conditions.

AB - A short-step route to GlcNAc-Cbz-Asn was developed. Treatment of GlcNAc in sat. aq. NH4HCO3 solution and subsequent electorodialytic desalting provided ammonia-free glycosylamine in large quantity. The product was coupled with Cbz-Asn α-isobutyl ester β-fluoride, and finally, the isobutyl ester was deprotected by enzyme-catalyzed hydrolysis under mild conditions.

KW - Amino acids

KW - Coupling

KW - Enzymes

KW - Glycosides

KW - Hydrolyses

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An expeditious route to GlcNAc-Cbz-Asn by chemo-enzymatic synthesis

Abstract

Keywords

ASJC Scopus subject areas

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