Preparation of (E)- and (Z)-2-methyl-2-butenoic acids

Details Preparation of (E)- and (Z)-2-methyl-2-butenoic acids Preparation of (E)- and (Z)-2-methyl-2-butenoic acids

2007-10-23

2007-10-23

Ramirez, Delia M. (Department: 1652)

Chemistry: molecular biology and microbiology

Micro-organism, per se ; compositions thereof; proces of...

Bacteria or actinomycetales; media therefor

C435S227000, C435S018000, C435S320100, C435S232000, C536S023200, C530S350000

Reexamination Certificate

active

11585036

ABSTRACT:
A method has been developed to prepare (E)- and (Z)-2-methyl-2-butenoic acids (2M2BA) from a mixture of (E,Z)-2-methyl-2-butenenitriles (2M2BN) by the regioselective hydrolysis of (E)-2M2BN to (E)-2-methyl-2-butenoic acid (2M2BA) using enzyme catalysts having either a nitrilase activity or a combination of nitrile hydratase and amidase activities. The method provides high yields without significant conversion of (Z)-2M2BN to (Z)-2M2BA. The regioselective hydrolysis of (E)-2M2BN to (E)-2M2BA makes possible the facile separation of (E)-2M2BA from (Z)-2M2BN or (Z)-2-methyl-2-butenamide (2M2BAm), and the subsequent conversion of (Z)-2M2BN or (Z)-2M2BAm to (Z)-2M2BA.

REFERENCES:
patent: 5041646 (1991-08-01), Gebauer
patent: 5998180 (1999-12-01), Armitage et al.
patent: 2103616 (1994-02-01), None
patent: WO 03/000640 (2003-01-01), None
patent: WO 03/14356 (2003-02-01), None
Franz Effenberger et al., Tetrahedron: Asymmetry, 12:2581-2587 (2001), (G)-Selective hydrolysis of (E,Z)-alpha, Beta-unsaturated nitriles by the recombinant nitrilase AINIT1 fromArabidopsis thaliana.
Robert E. Buckles et al., J. Org. Chem., 15:680-684 (1950), The Preparation of Tiglic and Angelic Acids and Esters.
H. Alper et al., Tetrahedron Lett. 30(20):2815-2816, 1969, Stereospecific Nickel and Phase Transfer Catalyzed Carbonylation of Vinyl Bromides and Chlorides.
S. W. Pelletier et al., J. Am. Chem. Soc., 74:6292-6293, 1952, The Ultraviolet-induced Isomerization of Tiglic Acid to Agnelic Acid.
Michihiko Kobayashi et al., Tetrahedron 46:5587-5590, 1990, Monohydrolysis of an Aliphatic Dinitrile Compound by Nitrilase fromRhodococcus rhodochrousK22.
Michihiko Kobayashi et al., J. Bacteriology, 172:4607-4615, 1990, Purification and Cahracterization of a Novel Nitrilase ofRhodococcus rhodochrousK22 That Acts on Aliphatic Nitriles.
S. Levy-Schil et al., Gene, 161;15-20, 1995, Aliphatic nitrilase from a soil-isolatedComamones testosteronisp.:gene cloning and overexpression, purification and primary structure.
John E. Gavagan et al., J. Org. Chem., 63:4792-4801, 1998, Chemoenzymic Production of Lactame from Aliphatic alpha, w-Dinitriles.
Don Cowen et al., Extremophiles, 2:207-216, 1998, Biochemistry and biotechnology of mesophilic and thermophilic nitrile metabolizing enzymes.
Sheng-Min Zhao et al., Chinese J. Chem., 20:1291-1299, 2000, Synthesis of Optically Active beta-Alkyl-alpha-methylane-y-butyro-lactones from Enantioselective Biotransformation of Nitriles, an Unusual Inversion of Enantioselectivity.
Qadrayah A. Almatawah et al., Extremephiles, 3:283-291, 1999, Characterization of an inducible nitrilase from a thermophilic bacillus.
Masahiro Miura et al., J. Chem. Soc., Perkin Transactions 1 (1):73-76, 1989, Carbonylation of Vinyl Halides with Caronbylcobalt.
Michihiko Kobayashi et al., Eur. J. Biochem., vol. 217:327, 1993, Amidase coupled with low-molecular-mass nitrile hydratase fromRhodococcus rhodochrousJ1.
Ludmila Martinkova et al., Biocatalysis and Biotransformation 20:73-93 (2002). Nitrile-and Amideconverting Microbial Enzymes: Stereo-, Regio- and Chemoselectivity.
Branden et al., Introduction to Protein Structure, Garland Publishing Inc., new York, p. 247, 1991. Prediction, Engineering, And Design of Protein Structures.
Jennifer L. Seffernick et al., Journal of Bacteriology, vol. 163(6):2405-2410, 2001, Melamine Deaminase and Atrazine Chlorohydrolase: 98 Percent Identical but Functionally Different.
Andrzaj Witkowski et al., Biochemistry, vol. 38:11643-11650, 1999, Conversion of a beta-Ketoacyl Synthase to a Malonyl Decarboxylase by Replacement of the Active-Site Cystine with Glutamine.

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