Eight stereoisomers of homonojirimycin from D-mannose

Gabriel M J Lenagh-Snow; Sarah F Jenkinson; Scott J Newberry; Atsushi Kato; Shinpei Nakagawa; Isao Adachi; Mark R Wormald; Akihide Yoshihara; Kenji Morimoto; Kazuya Akimitsu; Ken Izumori; George W J Fleet

doi:10.1021/ol3005744

Eight stereoisomers of homonojirimycin from D-mannose

Org Lett. 2012 Apr 20;14(8):2050-3. doi: 10.1021/ol3005744. Epub 2012 Apr 3.

Authors

Gabriel M J Lenagh-Snow¹, Sarah F Jenkinson, Scott J Newberry, Atsushi Kato, Shinpei Nakagawa, Isao Adachi, Mark R Wormald, Akihide Yoshihara, Kenji Morimoto, Kazuya Akimitsu, Ken Izumori, George W J Fleet

Affiliation

¹ Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, OX1 3TA, UK.

PMID: 22472134
DOI: 10.1021/ol3005744

Abstract

Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.

Publication types

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

MeSH terms

1-Deoxynojirimycin / analogs & derivatives*
1-Deoxynojirimycin / chemical synthesis
1-Deoxynojirimycin / chemistry
Euphorbiaceae / chemistry
Mannose / chemistry*
Molecular Structure
Stereoisomerism

Substances

homonojirimycin
1-Deoxynojirimycin
Mannose