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 X. Santarelli and D. 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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References

SHOWING 1-10 OF 11 REFERENCES
Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments.
TLDR
The method described, which is the first allowing the direct synthesis of aromatic acid esters of flavonoid glucoside, can be applied to the acylation of other glucosides, including naringin, rutin, callistephin, and chrysanthemin. Expand
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.Expand
Use of Mucor miehei lipase in the preparation of long chain 3-O-acylcatechins
Long chain 3-O-acylcatechins were prepared in high yield by alcoholysis with n-butanol of the corresponding pentaacylderivatives in the presence of lipase from Mucor miehei (immobilised, Lipozyme®Expand
Modification of flavonoid using lipase in non-conventional media: effect of the water content.
TLDR
The enzymatic acylation of a flavonoid (naringin) was investigated in this work and the effect of the initial hydration level of the reaction medium components was pointed out for naringin palmitate synthesis. Expand
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 benzylmalonylExpand
Effect of different biochemical parameters on the enzymatic synthesis of fructose oleate
Enzymatic synthesis of sugar ester was performed using an immobilized Candida antartica lipase, fructose and oleic acid methyl ester as substrates and 2-methyl 2-butanol as a solvent. The influenceExpand
Enzymatic synthesis of fatty acid ascorbyl esters
Abstract Lipase B from the yeast Candida antartica was used to catalyze the enzymatic synthesis of fatty acid ascorbyl esters, in 2-methyl-2-butanol as a solvent. The influence of water activity ( aExpand
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. Expand
Lipase-catalyzed α-butylglucoside lactate synthesis in organic solvent for dermo-cosmetic application
Abstract α -Butylglucoside can be used as a vector for lactic acid: α -butylglucoside lactate synthesis can be achieved through transesterification catalyzed by immobilized Candida antarctica lipase.Expand
Study of Citrus taitensis and radical scavenger activity of the flavonoids isolated
Abstract The GC-MS study of the head space volatiles of Citrus taitensis Risso revealed that the main component, constituting 60% of the oil, is linalool. Three N-containing compounds, benzylExpand
...
1
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