Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine

AT Carmona, Richard Wightman, I Robina, P Vogel

Research output: Contribution to journalArticle

Abstract

Reaction of 1,4-anhydro-2,3,5-tri-O-benzyl-1-deoxy-1-imino-D-arabinitol N-oxide (8) with allyl alcohol produced a 3.6:1 mixture of the two pyrrolo[1,2-b]isoxazole derivatives 13 and 14. The major adduct 13 was converted to 7-deoxycasuarine (7), a potent, specific, and competitive inhibitor of amyloglucosidase from Rhizopus mold (see Table).

Original languageEnglish
Pages (from-to)3066-3073
Number of pages8
JournalHelvetica Chimica Acta
Volume86
Issue number9
DOIs
Publication statusPublished - 2003

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Isoxazoles
Glucan 1,4-alpha-Glucosidase
Glycoside Hydrolases
Oxides
Derivatives
allyl alcohol
arabitol

Cite this

Carmona, AT ; Wightman, Richard ; Robina, I ; Vogel, P. / Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine. In: Helvetica Chimica Acta. 2003 ; Vol. 86, No. 9. pp. 3066-3073.
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Carmona, AT, Wightman, R, Robina, I & Vogel, P 2003, 'Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine', Helvetica Chimica Acta, vol. 86, no. 9, pp. 3066-3073. https://doi.org/10.1002/hlca.200390248

Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine. / Carmona, AT; Wightman, Richard; Robina, I; Vogel, P.

In: Helvetica Chimica Acta, Vol. 86, No. 9, 2003, p. 3066-3073.

Research output: Contribution to journalArticle

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AU - Carmona, AT

AU - Wightman, Richard

AU - Robina, I

AU - Vogel, P

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