Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Hydrolase
Patent
1997-08-13
1998-09-29
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Enzyme , proenzyme; compositions thereof; process for...
Hydrolase
435121, 435232, 4352521, 435122, C12N 978, C12N 988, C12P 1710, C12P 1712
Patent
active
058145087
ABSTRACT:
A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrile-carboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.
REFERENCES:
patent: 4329498 (1982-05-01), Demmin et al.
patent: 4599199 (1986-07-01), Fuchs
patent: 4730040 (1988-03-01), Vagt et al.
patent: 5449780 (1995-09-01), Kosak
patent: 5705382 (1998-01-01), Endo et al.
Chemical Abstracts 113:230773k Cushman et al "Synth. Commun" Dec. 17, 1990 20(10) 1463-8.
Chemical Abstracts 94:14593y Bargar et al "Synth. Commun" 1980 10(6)479-87, Jan. 19, 1981.
Chemical Abstracts 119:225898z Lange et al "Synth Commun" Nov. 22, 1993 23 (10) 1371-77.
Kobayashi, et al., Tetrahedron, vol. 46, 5587-5590 (1990).
Kobayashi, et al., J. Bacteriology, vol. 172, 4807-4815 (1990).
Levy-Schil, S., et al., Gene, vol. 161, 15-20 (1995).
Gradley, M.L. and Knowles, C.J., Biotechnology Lett., vol. 16, 41-46 (1994).
Bengis-Garber, C. and Gutman, A.L., Appl. Microbiol. Biotechnol., vol. 32, 11-16 (1989).
Honicke-Schmidt, P. and Schneider, M.P., J. Chem. Soc., Chem. Commun., 648-650 (1990).
Blakely, A. J., et al., FEMS Microbiology Lett., vol. 129, 57-62 (1995).
Yamada, H., et al. J. Ferment. Technol., vol. 58, 495-500 (1980).
Yamamoto, K., et al. J. Ferment, Bioengineering, vol. 73, 125-129 (1992).
Moreau, J.L., et al. Biocatalysis, vol. 10, 325-340 (1994).
Kerridge, A., et al., Biorg. Medicinal Chem., vol. 2, 447-455 (1994).
Asano, Y., et al., Agric Biol. Chem., vol. 44, 2497-2498 (1980).
Taylor, E.C., et al., J. Am. Chem. Soc., vol. 87, 1984-1990 (1965).
Taylor, E.C., et al., J. Am. Chem. Soc., vol 87, 1990-1995 (1965).
Blade-Font, A., Tetrahedron Letters, vol. 21, 2443-2446 (1980).
Frank, R.L., et al., Org. Sytheses, Coll. vol. 3, 328-329 (1954).
Zienty, F.B. and Steahly, G.W., J. Am. Chem. Soc., vol. 69, 715-716 (1947).
Bargar et al., Rapid and Efficient Method for Dehydration of Primary Amides to Nitriles, Chemical Abstracts, 94, No. 3, Abstract No. 14593, Jan. 19, 1981.
M. Cushman et al., A. Synthesis of 2-alkyl and 2-benzyl Substituted Acrylonitriles from 2-alkyl and 2-benzylidenecyanoacetate Esters under Mild Conditions, Chemical Abstracts, 113, No. 25, Abstract No. 230773, Dec. 17, 1990.
J. Lange et al., Direct Pyradazine Ring Synthesis from Beta-cyano Esters, Chemical Abstracts, 119, No. 21, Abstract No. 225898, Nov. 22, 1993.
Di Cosimo Robert
Fallon Robert Donald
Gavagan John Edward
Herkes Frank Edward
E. I. Du Pont de Nemours and Company
Lilling Herbert J.
LandOfFree
Preparation of lactams from aliphatic .alpha.,.omega.-dinitriles 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 lactams from aliphatic .alpha.,.omega.-dinitriles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of lactams from aliphatic .alpha.,.omega.-dinitriles will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-685603