Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Reexamination Certificate
2007-04-03
2007-04-03
Ramirez, Delia M. (Department: 1652)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
C435S128000, C435S176000, C435S177000, C435S174000, C435S252300, C435S252330, C435S320100, C435S227000, C435S018000, C435S280000, C536S023200, C530S350000
Reexamination Certificate
active
10431965
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 03/000840 (2003-01-01), None
patent: WO 03/014355 (2003-02-01), None
Branden et al., Introduction to Protein Structure, Garland Publishing Inc., New York, p. 247, 1991.
Witkowski et al., Biochemistry 38:11643-11650, 1999.
Seffernick et al., J. Bacteriol. 183(8):2405-2410, 2001.
Franz Effenberger et al. , Tetrahedron: Asymmetry, 12:2581-2587 (2001), (E)- Selective hydrolysis of (E,Z)-α, β-unsaturated nitriles by the recombinant nitrilase AtNIT1 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 er et al., Tetrahedron Lett., 30(20):2615-2616 (1989), 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 Angelic 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, 172:4807-4815 (1990), Purification and Characterization 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-isolatedComamonas testosteronisp.: gene cloning and overexpression, purification and primary structure.
John E. Gavagan et al., J. Org.Chem., 63:4792-4801 (1998), Chemoenzymic Production of Lactams from Aliphatic α, ω-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 β-Alkyl-α-methylene-γ-butyro-lactones from Enantioselective Biotransformation of Nitriles, an Unusual Inversion of Enantioselectivity.
Qadreyah A. Almatawah et al., Exremphiles, 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 Carbonylcobalt.
Michihiko Kobayashi et al., Eur. J. Biochem., 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 Amide-converting Microbial Enzymes: Stereo-, Regio- and Chemoselectivity.
Bramucci Michael G.
Chauhan Sarita
Dicosimo Robert
Fallon Robert D.
Gavagan John E.
E. I. du Pont de Nemours and Company
Ramirez Delia M.
LandOfFree
Preparation of ( E )- and ( Z )-2-methyl-2-butenoic acids does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation of ( E )- and ( Z )-2-methyl-2-butenoic acids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of ( E )- and ( Z )-2-methyl-2-butenoic acids will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3778858