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^*

^*この論文の責任著者

薬剤部

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

9 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	4029-4033
ページ数	5
ジャーナル	Organic Letters
巻	23
号	10
DOI	https://doi.org/10.1021/acs.orglett.1c01248
出版ステータス	出版済み - 2021/05/21

ASJC Scopus 主題領域

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.1c01248

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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",

month = may,

day = "21",

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

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TY - JOUR

T1 - Synthesis and Structural Revision of Glyphaeaside C

AU - Byatt, Brendan J.

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.

UR - http://www.scopus.com/inward/record.url?scp=85106502287&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c01248

DO - 10.1021/acs.orglett.1c01248

M3 - 学術論文

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AN - SCOPUS:85106502287

SN - 1523-7060

VL - 23

SP - 4029

EP - 4033

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Synthesis and Structural Revision of Glyphaeaside C

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