Synthesis and Structural Revision of Glyphaeaside C

Brendan J. Byatt; Atsushi Kato; Stephen G. Pyne

doi:10.1021/acs.orglett.1c01248

Synthesis and Structural Revision of Glyphaeaside C

Brendan J. Byatt^*, Atsushi Kato, Stephen G. Pyne^*

^*Corresponding author for this work

Hospital Pharmacy

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

9 Scopus citations

Abstract

The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.

Original language	English
Pages (from-to)	4029-4033
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.1c01248
State	Published - 2021/05/21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis and Structural Revision of Glyphaeaside C",

abstract = "The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.",

author = "Byatt, {Brendan J.} and Atsushi Kato and Pyne, {Stephen G.}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

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doi = "10.1021/acs.orglett.1c01248",

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AU - Kato, Atsushi

AU - Pyne, Stephen G.

PY - 2021/5/21

Y1 - 2021/5/21

N2 - The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.

AB - The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.

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U2 - 10.1021/acs.orglett.1c01248

DO - 10.1021/acs.orglett.1c01248

M3 - 学術論文

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SN - 1523-7060

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SP - 4029

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JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Synthesis and Structural Revision of Glyphaeaside C

Abstract

ASJC Scopus subject areas

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