Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid

Stephen V. Evans; Alison R. Hayman; Linda E. Fellows; Tony K.M. Shing; Andrew E.Derome; George W.J. Fleet

doi:10.1016/S0040-4039(00)99072-5

Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid

Stephen V. Evans, Alison R. Hayman, Linda E. Fellows, Tony K.M. Shing, Andrew E.Derome, George W.J. Fleet

Department of Chemistry

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

55 Citations (Scopus)

Abstract

A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn. Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor free fagomine [1,2,5-trideoxy-1,5-imino-D-arabinohexitol] (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.

Original language	English
Pages (from-to)	1465-1468
Number of pages	4
Journal	Tetrahedron Letters
Volume	26
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(00)99072-5
Publication status	Published - 1985

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)99072-5

Fingerprint

Dive into the research topics of 'Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid'. Together they form a unique fingerprint.

Cite this

Evans, S. V., Hayman, A. R., Fellows, L. E., Shing, T. K. M., E.Derome, A., & Fleet, G. W. J. (1985). Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid. Tetrahedron Letters, 26(11), 1465-1468. https://doi.org/10.1016/S0040-4039(00)99072-5

Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid. / Evans, Stephen V.; Hayman, Alison R.; Fellows, Linda E. et al.
In: Tetrahedron Letters, Vol. 26, No. 11, 1985, p. 1465-1468.

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

Evans, SV, Hayman, AR, Fellows, LE, Shing, TKM, E.Derome, A & Fleet, GWJ 1985, 'Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid', Tetrahedron Letters, vol. 26, no. 11, pp. 1465-1468. https://doi.org/10.1016/S0040-4039(00)99072-5

Evans SV, Hayman AR, Fellows LE, Shing TKM, E.Derome A, Fleet GWJ. Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid. Tetrahedron Letters. 1985;26(11):1465-1468. doi: 10.1016/S0040-4039(00)99072-5

Evans, Stephen V. ; Hayman, Alison R. ; Fellows, Linda E. et al. / Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid. In: Tetrahedron Letters. 1985 ; Vol. 26, No. 11. pp. 1465-1468.

@article{a13190d3c13a42d9890dac7d4c5d736f,

title = "Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid",

abstract = "A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn. Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor free fagomine [1,2,5-trideoxy-1,5-imino-D-arabinohexitol] (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.",

author = "Evans, {Stephen V.} and Hayman, {Alison R.} and Fellows, {Linda E.} and Shing, {Tony K.M.} and Andrew E.Derome and Fleet, {George W.J.}",

year = "1985",

doi = "10.1016/S0040-4039(00)99072-5",

language = "English",

volume = "26",

pages = "1465--1468",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "11",

}

TY - JOUR

T1 - Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid

AU - Evans, Stephen V.

AU - Hayman, Alison R.

AU - Fellows, Linda E.

AU - Shing, Tony K.M.

AU - E.Derome, Andrew

AU - Fleet, George W.J.

PY - 1985

Y1 - 1985

N2 - A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn. Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor free fagomine [1,2,5-trideoxy-1,5-imino-D-arabinohexitol] (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.

AB - A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn. Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor free fagomine [1,2,5-trideoxy-1,5-imino-D-arabinohexitol] (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.

UR - http://www.scopus.com/inward/record.url?scp=46549098825&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=46549098825&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)99072-5

DO - 10.1016/S0040-4039(00)99072-5

M3 - Article

AN - SCOPUS:46549098825

SN - 0040-4039

VL - 26

SP - 1465

EP - 1468

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this