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Syntheses of dopa glycosides using glucosidases

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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, β-glucosidase isolated from sweet almond and immobilized β-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-C1β and d-sorbitol 8 to give 4-O-C6-O-arylated product. β-Glucosidase exhibited selectivity with d-mannose 4 to give 4-O-C1β and lactose 7 to give 4-O-C1β product. Immobilized β-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-(β-d-galactopyranosyl-(1′→4)β-d-glucopyranosyl) phenylalanine 16 at 0.9 ± 0.05 mM and dl-3-hydroxy-4-O-(β-d-glucopyranosyl) phenylalanine 11b,c at 0.98 ± 0.05 mM showed the best IC50 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 IC50 values for ACE inhibition.

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Acknowledgements

One of us (SD) acknowledges the Department of Biotechnology, India, for the financial assistance provided. TP also acknowledges DBT for the Project Assistantship provided. RS thanks the Council of Scientific and Industrial Research, New Delhi, India, for providing a Senior Research Fellowship.

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Authors and Affiliations

  1. Fermentation Technology and Bioengineering Department, Central Food Technological Research Institute, Council of Scientific and Industrial Research, Mysore, 570020, India

    Ramaiah Sivakumar, Thangavel Ponrasu & Soundar Divakar

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  1. Ramaiah Sivakumar
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  2. Thangavel Ponrasu
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  3. Soundar Divakar
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Corresponding author

Correspondence to Soundar Divakar.

Electronic supplementary material

Spectral data of all the synthesized glycosides are shown as supplementary data.

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Sivakumar, R., Ponrasu, T. & Divakar, S. Syntheses of dopa glycosides using glucosidases. Glycoconj J 26, 199–209 (2009). https://doi.org/10.1007/s10719-008-9176-y

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