Syntheses of dopa glycosides using glucosidases
IR@CFTRI: CSIR-Central Food Technological Research Institute, Mysore
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| Relation |
http://ir.cftri.com/8863/
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| Title |
Syntheses of dopa glycosides using glucosidases
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| Creator |
Ramaiah, Sivakumar
Thangavel, Ponrasu Soundar, Divakar |
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| Subject |
05 Enzymes
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| Description |
Syntheses of L-dopa 1a glucoside 10a,b and DLdopa
1b glycosides 10–18 with D-glucose 2, D-galactose 3,
D-mannose 4, D-fructose 5, D-arabinose 6, lactose 7, Dsorbitol
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-Dsorbitol)
phenylalanine 17 at 0.56±0.03 mM, L-dopa-Dglucoside
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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| Date |
2008
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Language |
en
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| Identifier |
http://ir.cftri.com/8863/1/Glycoconj_J.pdf
Ramaiah, Sivakumar and Thangavel, Ponrasu and Soundar, Divakar (2008) Syntheses of dopa glycosides using glucosidases. Glycoconjugate Journal, 26. pp. 33-39. ISSN 0282-0080 |
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