Enantio- and regioselective synthesis of organic compounds using

Details Enantio- and regioselective synthesis of organic compounds using Enantio- and regioselective synthesis of organic compounds using

1989-08-24

1992-04-21

Elmore, Carolyn

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435134, 435135, C12P 4100

Patent

active

051067501

ABSTRACT:
A process for irreversible regio- and stereoselective enzyme catalyzed acylation of alcohols using enol esters as acylating reagents is disclosed. The present invention permits the selective modification of hydroxyl group(s) of chiral and meso alcohols, including sugars, organometallics, and glycosides. The enol freed upon transesterification rapidly tautomerizes to the corresponding volatile aldehyde or ketone thereby preventing the reverse reaction from occurring.

REFERENCES:
patent: 4511655 (1985-04-01), Minai et al.
patent: 4607013 (1986-08-01), Mitsuda et al.
patent: 4916074 (1990-04-01), Yoshida et al.
patent: 4933290 (1990-06-01), Cesti et al.
patent: 4957867 (1990-09-01), Minai et al.
Therisod et al, Facile Enzymatic Preparation of Monoacylated etc., J. Am. Chem. Soc., 108, 5638-5640, Apr. 1986.
Riva et al, Protease-Catalyzed Regioselective etc., J. Am. Chem. Soc., 110 (2), 584-589, Jan. 1988.
Degueil-Castaing, M. Enzymatic Reactions in Organic Synthesis: etc., Tet. Let., 28 (9), 953-954, Sep. 1987.
Sweers et al, Enzyme-Catalyzed Regioselective Deacylation of etc., J. Am. Chem. Soc., 108, 6421-6422, May 1986.
Wang et al, Lipase Catalyzed Irreversible etc., J. Org. Chem., 53, 3127-3129, Feb. 1988.
Gil et al, Lipase-Catalyzed Ester Formation in Organic etc., Tet. Let., 28 (15), 1647-1648, 1987.
Ramos Tombo et al, Synthesis of Both Enantiomeric Forms of etc., Tet. Let., 27 (47), 5707-5710, Aug. 1986.
J. Bryan Jones, Enzymes in Organic Synthesis, Tetrahedron, 42 (13), 3351-3403, 1986.
Mitsunobu et al, Preparation of Carboxylic Esters and etc., Bull Chem. Soc. Japan, 44, 3427-3430, May 1971.
Mitsunobu et al, Stereospecific and Stereoselective Reactions. etc., JACS, 94 (2), 679-680, Jan. 1972.
Mitsunobu et al, Preparation of Esters of Carboxylic and etc., Bull Chem. Soc. Japan, 40 (10), 2380-2382, Feb. 1967.
Whitesides et al, Enzymes as Catalysts in Synthetic Organic etc., Ange. Chem., 24 (8), 617-718, Aug. 1985.
Rothman et al, Acid-Catalyzed Interchange Reactions of etc., J. Org. Chem., 27, 2123-3127, Sep. 1962.
Butt et al, Opportunities for Using Enzymes in Organic etc., Chem. in Britian, 127-134, Feb. 1987.
Akiyama et al, Enzymes in Organic Synthesis, Chem. in Britian, 645-654, Jul. 1987.
Klibanov, A., Enzymes that Work in Organic Solvents, Chemtech, 354-359, Jun. 1986.
Chen, C-H et al, Quantitative Analyses of Biochemical Kinetic etc., J. Am. Chem. Soc., 109 (9), 2812-2817, 1987.
Zhi-Wei et al, Enzymatic Synthesis of Macrocyclic Lactones, J. Am. Chem. Soc., 110 (6), 1999-2001, Mar. 1988.
Yokozeki et al, Application of Immobilized Lipase to etc., Eur. J. App. Microbiol. Biotech., 14, 1-5, 1982.
Belan et al, Use of Biological Systems for the Preparation etc., J. Org. Chem., 52 (2), 256-260, Feb. 1987.
Swern et al, Vinyl Laurate and other Vinyl Esters, Org. Synth., IV, 977-980, 1963.
Wang, Y-F et al, Bifunctional Chiral Synthons via Biochemical etc., J. Am. Chem. Soc., 106, 3695-3696, 1984.
Wang Y-F, Bifunctional Chiral Synthons via Biochemical etc., Tet. Let., 25 (44), 4999-5002, Jan. 1984.
Suemune et al, Enzymatic Synthesis of etc., Chem. Phar. Bull., 34 (8), 3440-3444, Feb. 1986.
Hirth et al, Synthesis of Glyceryletherphosphatides (Title etc. Helv. Chim. Acta, 65 (3), 1059-1084, 1982.
Stork et al, Stereospecific Reductive Methylation via a etc., J. Am. Chem. Soc., 108 (21), 6826-6828, Apr. 1986.
Mori et al, Synthesis and Bioactivity of Optically Active etc., Tetrahedron, 43 (10), 2249-2254, Oct. 1987.
Durrwachter et al, Fructose 1,6-Diphosphate Aldolase Catalyzed etc., J. Org. Chem., 53, 1018, Mar. 1988.
Stokes et al, Enzyme Reactions in Apolar Solvents: The etc., Tet. Let., 28 (19), 2091-2084, Dec. 1987.
Gokel et al, The Retentive Nucleophilic Displacements of etc., J. Org. Chem., 37 (20), 3052-3058, Mar. 1972.
Langrand et al, Lipase Catalyzed Reactions and Strategy for etc., Tet. Let., 27 (1), 29-32, 1986.
Cambou et al, Preparative Production of Optically Active etc., J. Am. Chem. Soc., 106 (9), 2687-2692, Apr. 1984.

Affiliated with

Also associated with

Rating

Enantio- and regioselective synthesis of organic compounds using does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Enantio- and regioselective synthesis of organic compounds using, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Enantio- and regioselective synthesis of organic compounds using will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1585563