Synthesis of (+)- and (-)-nojirimycin and their 1-deoxyderivatives from myo-inositol

Noritaka Chida, Yuka Furuno, Hiroyuki Ikemoto, Seiichiro Ogawa

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The conversion of the naturally abundant cyclitol, myo-inositol (4), into (+)-nojirimycin (la), its enantiomer (1b), and their 1-deoxy analogues (2a and 2b) is described. Biological assay of 2a, 2b, and the bisulfite adducts of 1a and 1b (3a and 3b) showed that the compounds having the unnatural l-gluco configuration (2b and 3b) possess moderate-to-high inhibitory activity against almond β-d-glucosidase and bovine liver β-d-galactosidase.

Original languageEnglish
Pages (from-to)185-194
Number of pages10
JournalCarbohydrate Research
Volume237
Issue numberC
DOIs
Publication statusPublished - 1992 Dec 31

Fingerprint

Cyclitols
Galactosidases
Glucosidases
Enantiomers
Inositol
Biological Assay
Liver
Assays
hydrogen sulfite
nojirimycin
Prunus dulcis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of (+)- and (-)-nojirimycin and their 1-deoxyderivatives from myo-inositol. / Chida, Noritaka; Furuno, Yuka; Ikemoto, Hiroyuki; Ogawa, Seiichiro.

In: Carbohydrate Research, Vol. 237, No. C, 31.12.1992, p. 185-194.

Research output: Contribution to journalArticle

Chida, Noritaka ; Furuno, Yuka ; Ikemoto, Hiroyuki ; Ogawa, Seiichiro. / Synthesis of (+)- and (-)-nojirimycin and their 1-deoxyderivatives from myo-inositol. In: Carbohydrate Research. 1992 ; Vol. 237, No. C. pp. 185-194.
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