Revised structure of a homonojirimycin isomer from Aglaonema treubii: first example of a naturally occurring alpha-homoallonojirimycin

O R Martin; P Compain; H Kizu; N Asano

doi:10.1016/s0960-894x(99)00551-x

Revised structure of a homonojirimycin isomer from Aglaonema treubii: first example of a naturally occurring alpha-homoallonojirimycin

Bioorg Med Chem Lett. 1999 Nov 1;9(21):3171-4. doi: 10.1016/s0960-894x(99)00551-x.

Authors

O R Martin¹, P Compain, H Kizu, N Asano

Affiliation

¹ Institut de Chimie Organique et Analytique (I.C.O.A.), Faculté des Sciences, Orléans, France. Olivier.Martin@univ-orleans.fr

PMID: 10560746
DOI: 10.1016/s0960-894x(99)00551-x

Abstract

The structure of a homonojirimycin isomer isolated from Aglaonema treublii and originally proposed as alpha-3,4-di-epi-homonojirimycin was revised to alpha-4-epi-homonojirimycin 3 ("alpha-homoallonojirimycin") on the basis of NMR analysis and synthetic studies. Its activity as a glycosidase inhibitor is compared to that of other homonojirimycin isomers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

1-Deoxynojirimycin / analogs & derivatives
Aza Compounds / chemical synthesis*
Carbohydrate Conformation
Carbohydrates / chemistry
Enzyme Inhibitors / chemical synthesis*
Glycoside Hydrolases / antagonists & inhibitors
Imino Pyranoses
Magnetic Resonance Spectroscopy
Molecular Structure
Piperidines / chemical synthesis*
Piperidines / chemistry*
Plant Extracts / chemistry
Structure-Activity Relationship

Substances

Aza Compounds
Carbohydrates
Enzyme Inhibitors
Imino Pyranoses
Piperidines
Plant Extracts
homonojirimycin
1-Deoxynojirimycin
Glycoside Hydrolases