Synthesis of Water‐Soluble Retinol Derivatives by Enzymatic Method
- 1 January 2002
- journal article
- Published by Wiley in Biotechnology Progress
- Vol. 18 (3) , 424-428
- https://doi.org/10.1021/bp025508f
Abstract
Retinoids (vitamin A and derivatives) are of great commercial potential in cosmetics and pharmaceuticals such as skin care products. However, the clinical effectiveness of these retinoids is limited by skin irritation, water insolubility, and except for retinyl‐esters, extreme instability. In this paper, an enzymatic method for preparing water‐soluble retinol derivatives catalyzed by immobilized lipase is described. The synthesis is based on a unique strategy of two‐step enzymatic acylation. Among the different synthesized compounds, the most water‐soluble are the disaccharide derivatives such as saccharose retinyl adipate (nonionic water‐soluble retinol derivative) and the sodium salt of retinyl diacids such as retinyl succinate sodium salt (ionic water‐soluble retinol derivative).Keywords
This publication has 15 references indexed in Scilit:
- Study of Vitamin Ester Synthesis by Lipase-Catalyzed Transesterification in Organic MediaBiotechnology Progress, 2000
- Production and in situ separation of mono- or diacylglycerol catalyzed by lipases in n-hexaneEnzyme and Microbial Technology, 1995
- Atom/Fragment Contribution Method for Estimating Octanol–Water Partition CoefficientsJournal of Pharmaceutical Sciences, 1995
- Diet and dermatologyJournal of the American Academy of Dermatology, 1993
- Enzymes in the synthesis of chiral drugsEnzyme and Microbial Technology, 1993
- Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamideJournal of the American Chemical Society, 1988
- Peptide synthesis catalyzed by lipases in anhydrous organic solventsJournal of the American Chemical Society, 1987
- Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systemsJournal of the American Chemical Society, 1987
- Lipase catalyzed reactions and strategy for alcohol resolutionTetrahedron Letters, 1986
- Mechanism of action of retinoidsJournal of the American Academy of Dermatology, 1986