Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine

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).


Published in:
Helvetica Chimica Acta, 86, 9, 3066-3073
Year:
2003
ISSN:
0018-019X
Keywords:
Note:
Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain. Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland. Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland.
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Laboratories:




 Record created 2005-11-09, last modified 2018-01-27


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