Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure

@article{Passicos2004RegioselectiveAO,
  title={Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure},
  author={Emilie Passicos and Xavier Santarelli and Denis Coulon},
  journal={Biotechnology Letters},
  year={2004},
  volume={26},
  pages={1073-1076}
}
A single-step acylation of rutin and naringin, catalyzed by immobilized Candida antarctica lipase B in 2-methyl-2-butanol, occurred preferentially on the primary hydroxyl group. Using palmitic methyl ester as acyl donor, the acylation rate of naringin was 10-fold higher than that of rutin. Under optimal conditions, i.e. a molar ratio acyl donor/naringin of 7:1 and 200 mbar, 92% naringin was acylated. 
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This work describes the reaction of naringin withCastor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica, and determined the chemical structure of naredin 6″-ricinoleate, which was determined using NMR analysis.
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References

SHOWING 1-10 OF 11 REFERENCES
Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media
Flavonoid fatty esters were prepared by acylation of flavonoids (rutin and naringin) by fatty acids (C8, C10, C12), catalyzed by immobilized lipase from Candida antarctica in various solvent systems.
Modification of flavonoid using lipase in non-conventional media: effect of the water content.
A two-step efficient chemoenzymatic synthesis of flavonoid glycoside malonates.
A simple and high-yielding protocol for the malonylation of some flavonoid glycosides is described. The two-step synthesis is based on the regioselective enzymatic introduction of a benzylmalonyl
Enzymatic synthesis of fatty acid ascorbyl esters
Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters.
TLDR
This work demonstrates the feasibility of assembling complex flavonoid glycoside esters in just two steps by sequential use of commercially available glycosidases and lipases.
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