Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

Chintam Narayana; Priti Kumari; Daisuke Ide; Nasako Hoshino; Atsushi Kato; Ram Sagar

doi:10.1016/j.tet.2018.02.063

Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

Chintam Narayana, Priti Kumari, Daisuke Ide, Nasako Hoshino, Atsushi Kato, Ram Sagar^*

^*Corresponding author for this work

Hospital Pharmacy

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

10 Scopus citations

Abstract

An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.

Original language	English
Pages (from-to)	1957-1964
Number of pages	8
Journal	Tetrahedron
Volume	74
Issue number	15
DOIs	https://doi.org/10.1016/j.tet.2018.02.063
State	Published - 2018/04/12

Keywords

Carbasugar
Ferrier carbocyclization
Glycosidase inhibitors
N-acetyl glucosamine
Peterson olefination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2018.02.063

Cite this

@article{df4dbdffc99b4a8a91311484c2ab9191,

title = "Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors",

abstract = "An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.",

keywords = "Carbasugar, Ferrier carbocyclization, Glycosidase inhibitors, N-acetyl glucosamine, Peterson olefination",

author = "Chintam Narayana and Priti Kumari and Daisuke Ide and Nasako Hoshino and Atsushi Kato and Ram Sagar",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = apr,

day = "12",

doi = "10.1016/j.tet.2018.02.063",

language = "英語",

volume = "74",

pages = "1957--1964",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "15",

}

TY - JOUR

T1 - Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

AU - Narayana, Chintam

AU - Kumari, Priti

AU - Ide, Daisuke

AU - Hoshino, Nasako

AU - Kato, Atsushi

AU - Sagar, Ram

PY - 2018/4/12

Y1 - 2018/4/12

N2 - An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.

AB - An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity.

KW - Carbasugar

KW - Ferrier carbocyclization

KW - Glycosidase inhibitors

KW - N-acetyl glucosamine

KW - Peterson olefination

UR - http://www.scopus.com/inward/record.url?scp=85043326542&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.02.063

DO - 10.1016/j.tet.2018.02.063

M3 - 学術論文

AN - SCOPUS:85043326542

SN - 0040-4020

VL - 74

SP - 1957

EP - 1964

JO - Tetrahedron

JF - Tetrahedron

IS - 15

ER -

Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this