In connection with structural modification of the trehalase inhibitor trehazolin (1), as a new-type of glycohydrolase inhibitor, some glycosylamino-oxazolines were designed and synthesized. Among three oxazolines beta-galacto (3), beta-gluco (5) and alpha-manno-types (6) obtained in stable form, the
✦ LIBER ✦
Synthesis and Glycosidase Inhibitory Activity of 7-Deoxycasuarine
✍ Scribed by Ana T. Carmona; Richard H. Whigtman; Inmaculada Robina; Pierre Vogel
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- German
- Weight
- 133 KB
- Volume
- 86
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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).
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