Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: EC:3.4.15.1 (ACE)
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About 12 glycosides prepared through amyloglucosidase catalysis and 23 amino acyl esters of carbohydrates prepared through lipase catalysis in organic solvents showed angiotensin converting enzyme (ACE) inhibition activity. Both amino acyl esters of carbohydrates and glycosides exhibited IC50 values for ACE inhibition in the 0.5 mM to 15.7 mM range. Eugenyl-D-glucoside (IC50: 0.5+/-0.04 mM), L-isoleucyl-D-glucose (IC50: 0.7+/-0.067 mM), vanillyl-D-sorbitol (IC50: 0.8+/-0.09 mM), L-histidyl-D-fructose (IC50: 0.9+/-0.087 mM), L-tryptophanyl-D-fructose (IC50: 0.9+/-0.092 mM), octyl-D-glucoside (IC50: 1.0+/-0.093 mM), vanillyl-D-mannoside (IC50: 1.0+/-0.089 mM), L-valyl-D-mannitol (IC50: 1.0+/-0.092 mM) and L-phenylalanyl-D-glucose (IC50: 1.0+/-0.089 mM) were the compounds, which showed the best ACE inhibitory activities.
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PMID:Glycosides and amino acyl esters of carbohydrates as potent inhibitors of angiotensin converting enzyme. 1673 Mar 92

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 IC(50) values for antioxidant activity and DL: -3-hydroxy-4-O-(6-D: -sorbitol)phenylalanine 17 at 0.56 +/- 0.03 mM, L: -dopa-D: -glucoside 10a,b at 1.1 +/- 0.06 mM and DL: -3-hydroxy-4-O-(D: -glucopyranosyl)phenylalanine 11a-d at 1.2 +/- 0.06 mM exhibited the best IC(50) values for ACE inhibition.
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PMID:Syntheses of dopa glycosides using glucosidases. 1871 74