Methods for separating diol and triol stereoisomers from a stere

Details Methods for separating diol and triol stereoisomers from a stere Methods for separating diol and triol stereoisomers from a stere

1990-01-26

1992-11-24

Robinson, Douglas W.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing oxygen-containing organic compound

435134, 435280, C12P 762

Patent

active

051660628

ABSTRACT:
Methods of separating the stereoisomers of secondary di- and tri-alcoholic compounds comprise reacting a racemic mixture of the secondary alcohols with an acyl anhydride or an ester in the presence of an enzyme which stereoselectively acylates the (R) site of the alcohol to form the (R) site acyl ester of the alcohol and separating the (S,S) or (S,S,S) secondary alcohol, the (R,S) or (R,S,S) monoacyl ester of the alcohol, the (R,R) or (R,R,S) diacyl ester and/or the (R,R,R) triacyl ester of the alcohol from one another and from the reaction medium. Additional methods of separating the stereoisomers of a secondary di- or tri-alcohol comprise reacting a stereochemical mixture of acyl esters of the di- or tri-alcohol with an enzyme which selectively deacylates the (R) or (S) site of the secondary alcohol to produce (R) or (S) site deacylated isomers of the secondary alcohol and separating the free alcohol, the monoacyl ester, the diacyl ester, and the triacyl ester of the alcohol from one another and the reaction medium.

REFERENCES:
Wang, Y. F. et al., "Extending the Applicability of Esterases of Low Enantioselectivity in Asymmetric Synthesis", Enzymes in Organic Synthesis, Pittman, London pp. 128-145 1985.
Bianchi, D. et al., "Anhydrides as Acylating Agents in Lipase-Catalyzed Stereoselective Esterification of Racemic Alcohols", J. Org. Chem., vol. 53, pp. 5531-5334, 1988.
Koppenhoefer et al, J. Chromatog. 358:159 (1986).
Hemmerle et al, Tetrahedron Lett. 28:3471 (1987).
Ramos Tombo et al, Tetrahedron Lett. 27:5707 (1986).
Huang et al, J. Am. Chem. Soc. 97:14 (1975).
Chen et al, J. Sm. Chem. Soc. 103:3580 (1981).
Cambou et al, J. Am. Chem. Soc. 107:2687 (1984).
Zaks et al, Science 224:1249 (1984).
Gatfield, Annals N.Y. Acad. Sci. 568:(1984).
Zaks et al, PNAS (USA) 82:3192 (1985).
Klibanov, CHEMTECH 354 (1986).
Cambou et al, Biotechnology and Bioengineering 26:1449 (1984).
Kirchner et al, J. Am. Chem. Soc. 107:2072 (1985).
Langard et al, Tetrahedron Lett., 26:1857 (1985).
Langrand et al, Tetrahedron Lett., 27:29 (1986).
Gil et al, Tetrahedron Lett., 28:1647 (1987).
Bianchi et al, J. Org. Chem. 53:5531 (1988).
Francalanci et al, J. Org. Chem. 52:5079 (1987).

Affiliated with

Also associated with

Rating

Methods for separating diol and triol stereoisomers from a stere does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Methods for separating diol and triol stereoisomers from a stere, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods for separating diol and triol stereoisomers from a stere will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-921225