Enzyme‐Mediated Regioselective Acylations of Flavonoid Disaccharide Monoglycosides
作者： Bruno Danieli , Paolo De Bellis , Giacomo Carrea , Sergio Riva
关键词: Acylation 、 Quercetin 、 Chemistry 、 Stereochemistry 、 Rutin 、 Subtilisin 、 Glycoside 、 Naringin 、 Disaccharide 、 Flavonoid
摘要: Flavonoid disaccharide monoglycosides have been acylated by the catalytic action of protease subtilisin in anhydrous pyridine. The effects nature sugars and interglycosidic bonds on regioselectivity reactions analyzed. selectivity was excellent with rutin (1), hesperidin (2), naringin (6), quercetin 3-O-[O-(β-D-glucopyranosyl)-(14)-α-L-rhamnoside] (9), giving single monoesters their glucose moieties (see la, 2a, 6a, 9b, resp.); quite interestingly, last compound, acylation did not occur at free primary OH group but secondary OHC(3‴). On other hand, a mixture mono- diesters obtained flavonoid peltatoside (7).
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