Syntheses of dopa glycosides using glucosidases.

Glycoconjugate Journal
Ramaiah SivakumarSoundar Divakar

Abstract

Syntheses of L: -dopa 1a glucoside 10a,b and DL: -dopa 1b glycosides 10-18 with D: -glucose 2, D: -galactose 3, D: -mannose 4, D: -fructose 5, D: -arabinose 6, lactose 7, D: -sorbitol 8 and D: -mannitol 9 were carried out using amyloglucosidase from Rhizopus mold, beta-glucosidase isolated from sweet almond and immobilized beta-glucosidase. Invariably, L: -dopa and DL: -dopa gave low to good yields of glycosides 10-18 at 12-49% range and only mono glycosylated products were detected through glycosylation/arylation at the third or fourth OH positions of L: -dopa 1a and DL: -dopa 1b. Amyloglucosidase showed selectivity with D: -mannose 4 to give 4-O-C1beta and D: -sorbitol 8 to give 4-O-C6-O-arylated product. beta-Glucosidase exhibited selectivity with D: -mannose 4 to give 4-O-C1beta and lactose 7 to give 4-O-C1beta product. Immobilized beta-glucosidase did not show any selectivity. Antioxidant and angiotensin converting enzyme inhibition (ACE) activities of the glycosides were evaluated glycosides, out of which L: -3-hydroxy-4-O-(beta-D: -galactopyranosyl-(1'-->4)beta-D: -glucopyranosyl) phenylalanine 16 at 0.9 +/- 0.05 mM and DL: -3-hydroxy-4-O-(beta-D: -glucopyranosyl) phenylalanine 11b,c at 0.98 +/- 0.05 mM showed the best I...Continue Reading

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Citations

Sep 6, 2013·Journal of Industrial Microbiology & Biotechnology·Nguyen Huy Thuan, Jae Kyung Sohng

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