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Synthesis and Glycosidase Inhibitory Activity of 7‐Deoxycasuarine
Author(s) -
Carmona Ana T.,
Whigtman Richard H.,
Robina Inmaculada,
Vogel Pierre
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390248
Subject(s) - chemistry , isoxazole , stereochemistry , adduct , glycoside hydrolase , rhizopus , acetylation , inhibitory postsynaptic potential , organic chemistry , enzyme , biochemistry , fermentation , neuroscience , biology , gene
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 ).