Selective hydrolysis of saturated esters over unsaturated esters

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound

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435140, 435141, 435262, 435264, 523102, 526 77, C12P 740, C12P 754, C12P 752

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058561501

ABSTRACT:
Processes are disclosed for the selective hydrolysis of saturated esters, e.g., ethyl propionate, over unsaturated esters, e.g., ethyl acrylate, using enzymes, e.g., lipases. The processes are useful, for example, for removing undesired esters from monomer feeds used in latex polymerization and from the latexes after polymerization. The processes can be used, for example, to treat latexes used in hair fixative compositions to remove unpleasant odors.

REFERENCES:
patent: 4003865 (1977-01-01), Nowak et al.
patent: 4017364 (1977-04-01), van Leemputten
patent: 4283491 (1981-08-01), Dappen
patent: 4897352 (1990-01-01), Chonde et al.
patent: 5145890 (1992-09-01), Frederick
patent: 5422269 (1995-06-01), Nicks et al.
APS Abstract Japan 58-165796 Murase et al Sep. 30, 1983.
Waley, S.G., Mechanisms of Organic and Enzymic Reactions, Oxford University Press, London (1962), pp. 233-249.
Alvarez, F.J., Stella, V.J., Pharm. Res. 6(7), 555-63 (1989), "Pancreatic lipase-catalyzed hydrolysis of estersof hydroxymethyl phenytoin dissolved in various metabolizable vehicles, dispersed in micellar systems, and in aqueous suspensions."
Jones, J.B., Ann. N.Y. Acad. Sci. 501, 119-128 (1987), "Some examples of enzymes in organic synthesis."
Bell, G., Blain, J.A., Patterson, J.D.E., Shaw, C.E.L., Todd, R., FEMS Microbiology Letters 3, 223-225 (1978), "Ester and glyceride synthesis by Rhizopus arrhizus mycelia."
Oesterberg, E., Ristoff, C., Holmberg, K., Tenside, Surfactants, Deterg. 25(5), 293-7 (1988), "Lipase catalyzed hydrolysis."
Sanders, J.M., Burja, L.T., Matthews, H.B., Drug Metabolism and Disposition 16(3), 429-434 (1988), "Metabolism and disposition of n-butyl acrylate in male Fischer rats."
Salleh, A.B., Yunus, W.M., Abdul Rahman, R.N., Ibrahim, A., Proc. Malays. Biochem Soc. Conf., 12th, 26-9 (1986), "Poly(ethyl acrylate-divinylbenzene) as a matrix for coupling enzyme."
Bar-Eli, A., Katchalski, E., Nature 188(4753), 856-857 (Dec. 3, 1960), "A water-insoluble trypsin derivative and its use as a trypsin column."
Maxim, S., Flondor A., Revue Roumaine de Chimie 34(6), 1389-95 (1989), "New crosslinked functionalized acrylic copolymers for biotechnological applications."
Mattson, F.H, Volpenhein, R.A., J. Lipid Res. 10(3), 271-6 (1969), "Relative rates of hydrolysis by rat pancreatic lipase of esters of C2-18 fatty acids with C1-18 primary n-alcohols"-.
Quinn, D.M., Biochemistry 24(13), 3144-9 (1985), "Solvent isotope effects for lipoprotein lipase catalyzed hydrolysis of water-soluble p-nitrophenyl esters."
O'Connor, C.J., Mitha, A.S.GH., Aust. J. Chem. 39(2), 259-69 (1986), "Studies in bile salt solutions, XIV, Electronic, charge, and steric substrate-effects on the esterase activity of bile-salt-stimulated human milk lipase. Hydrolysis of 4-substituted phenyl propionates."
Wu, S.H., Guo, Z.W., Sih, C.J., J. Am. Chem. Soc. 112(5), 1990-5 (1990), "Enhancing the enantioselectivity of Candida lipase-catalyzed ester hydrolysis via noncovalent enzyme modification."
Cambou, B., Klibanov, A.M., J. Am. Chem. Soc. 106, 2687-2692 (1984), "Preparative production of optically active esters and alcohols using esterase-catalyzed sterospecific transesterification in organic media."
Cambou, B., Klibanov, A.M., Biotechnology and Bioengineering 26, 1449-1454 (1984), "Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols:asymmetric hydrolysis, esterification, and transesterification."
Cesti. P. Zaks, A. Klibanov, A.M., Applied Biochemistry and Biotechnology 11, 401-407 (1985), "Preparative regioselective acylation of glycols by enzymatic transesterification in organic solvents."
Dahl, A.R., Miller, S.C., Petridou-Fischer, J., Toxicology Letters 36, 129-136 (1987), "Carboxylesterases in the respiratory tracts of rabbits, rats and Syrian hamsters."
Klibanov, A.M., Samokhin, G.P., Martinek, K. Berezin, I.V., Biotechnology and Bioengineering 19, 1351-1361 (1977), "A new approach to preparative enzymatic synthesis."
Vidaluc, J.L., Baboulene, M. Speziale, V., Lattes, A. Tetrahedron 39(2), 269-274 (1983), "Optimization of the enzymatic synthesis of amino acid esters, reaction is polyphasic medium."
Heimermann, W.H. Holman, R.T. Gordon, D.T., Kowalyshyn, D.E., Jensen, R.G., Lipids 8(1), 45-7 (1973), "Effect of double bond position in octadecenoates upon hydrolysis by pancreatic lipase."
Tor, M. Chen. W., Bengtsson-Olivecrona, G., Aakesson, B., Nilson, A., Biochim. Biophys, Acta 1075(3), 259-66 (1991), "Hydrolysis of chylomicron polyenoic fatty acid esters with lipoprotein lipase and hepatic lipase."
Lie, E. Molin, G., J. Chem. Tech. Biotechnol. 50, 549-53 (1991), "Hydrolysis and esterification with immobilized lipase on hydrophobic and hydrophilic zeolites."
Corkill, J.A., Lloyd, E.J., Hoyle, P., Crout, D.H.G., Ling, R.S.M., James M.L., Piper R.J., Clin. Chim. Acta 68, 141-146 (1976), "Toxicology of methyl methacrylate: the rate of disappearance of methyl methacrylate in human blood in vitro."
Crout, D.H.G. Corkill, J.A. James, M.L. Ling, R.S.M, Clin. Orthop. Rel. Res. 141, 90-95 (1979), "The hydrolysis of methyl methacrylate to methacrylic acid during total hip replacement".
Miller, R.R., Ayres, J.A. Rampy, L.W. McKenna, M.J. Fundamental and Applied Toxicology 1, 410-14 (1981), "Metabolism of acrylate esters in rat tissue homogenates."
Klibanov, A.M., Siegel, E.H., Enzyme Microb. Technol. 4, 172-174 (1982), "Geometric specificity of porcine liver carboxylesterase and its application for the production of cis-arylacrylic esters."
Scott, W.T., McKenna, M.J., Fundamental and Applied Tosicology 5, 399-404 (1985), "Hydrolysis of several glycol ether acetates and acrylate esters by nasal mucosal carboxylesterase in vitro."
Ghanayem, B.I. Burka, L.T., Matthews, H.B., Fundamental and Applied Toxicology 9, 389-397 (1987), "Ethyl acrylate distribution, macromolecular binding, excretion, and metabolism in male Fisher 344 rats."
Silver, E.H., Murphy, S.D., Toxicol. Appl. Pharmacol. 57, 208-219 (1981), "Potentiation of acrylate ester toxicity by prior treatment with the carboxylesterase inhibitor triorthotolyl phosphate (TOTP)."
Vodicka, P. Gut, I. Frantik, E., Toxicology 65, 209-221 (1990), "Effects of inhaled acrylic acid derivatives in rats."
Tor, R., Dror, Y., Freeman, A., Enzyme Microb. Technol. 12, 299-304 (Apr., 1990), "Enzymatically catalyzed transesterification of acryl and methacryl monomeric esters."
McCarthy, T.J., and Witz, G., Adv. Exp. Med. Biol. 283, 333-335 (1991), "Structure-activity relationships of acrylate esters: Reactivity towards glutathione and hydrolysis by carboxylesterase in vitro."
Klibanov, A.M., Adv. Appl. Microb. 29, 1-28 (1983), "Stabilization of enzymes against thermal inactivation."
Tor, R., Dror, Freeman, A., Enzyme Microb. Technol. 11, 306-312 (1989), "Enzyme stabilization by bilayer encagement."
Weetall, H.H., Immobilized enzymes for industrial reactors (ed. R.A. Messing), Academic Press, New York (1975), chapter 6, pp. 99-123, "Immobilization by covalent attachment and by entrapment."
Kitano, H., Nakamura, K., Ise, N.J. of Applied Biochemistry 4, 487-95 (1982), "Functionalized polymer latices."
Bahadur, A., Bahadur, P., Indian J. of Biochemistry & Biophysics 22, 107-110 (Apr. 1985), "Trypsin immobilization on anionic polymeric latex."

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