Method of making poly(sugar acrylates) using hydrolytic enzymes

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

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435 95, 435 99, 435101, 435135, 536115, 536116, 536119, 536120, 536122, 536124, 536126, C12P 1900, C08F 200, C08F 1804, C07H 1300

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054749158

ABSTRACT:
A poly(sugar acrylate) is prepared by reacting vinyl acrylate with a sugar in the presence of hydrolytic enzymes to prepare an acryloyl ester of the sugar. The acryloyl ester of the sugar is then polymerized to form the poly(sugar acrylate). Useful hydrolytic enzymes include alkaline protease, aminoacylase, fungal amylase, bacterial protease, lipase from Pseudomonas cepacia and subtilisin. Useful sugars include .alpha.- or .beta.-alkyl- or .alpha.- or .beta.-halo-glycosides, sucrose, fructose, mannose, trehalose, raffinose, lactose and maltose. A free radical initiator can be used in the polymerization. A copolymer can be formed by mixing the sugar ester with a monomer such as 2-hydroxyethyl methacrylate before polymerizing. During formation of the copolymer, a cross-linking agent such as ethylene glycol dimethacrylate may be present. The poly(sugar acrylates) form hydrogels which are useful in absorbent materials such as diaper liners, packaging materials and drug delivery polymers.

REFERENCES:
patent: 3225012 (1965-12-01), Black et al.
patent: 3261814 (1966-07-01), Friedman
patent: 3265641 (1966-08-01), Wismer et al.
patent: 3400107 (1968-09-01), Black et al.
patent: 3483083 (1969-12-01), Elson et al.
patent: 4797481 (1989-01-01), Garlisi et al.
patent: 4877871 (1989-10-01), Klemann et al.
patent: 4952687 (1990-08-01), Bodor et al.
patent: 5006648 (1991-04-01), Van der Plank et al.
patent: 5024942 (1991-06-01), Shimizu et al.
patent: 5128248 (1992-07-01), Dordick et al.
patent: 5141860 (1992-08-01), Bornemann et al.
Chemical Abstracts 95(22): 188078v (1981).
Chemoenzymatic Synthesis of Novel Sucrose-Containing Polymers, Damodar R. Patil, Jonathan S. Dordick, and David G. Rethwisch, Dept. of Chemical and Biochemical Engineering, University of Iowa, Iowa City, Iowa.
Enzymatic Synthesis of a Sucrose-Containing Linear Polyester in Nearly Anhydrous Organic Media, Damodar R. Patil, David G. Rethwisch and Jonathan S. Dordick, Biotechnology and Bioengineering, vol. 37, pp. 639-646 (1991).
Substrate Structure and Solvent Hydrophobicity Control Lipase Catalysis and Enantioselectivity in Organic Media, Sanghamitra Parida and Jonathan S. Dordick, Journal of the American Chemical Society, 1991, 113.
Polymerization of Phenols Catalyzed by Peroxidase in Nonaqueous Media, Jonathan S. Dordick, Michael A. Marletta, and Alexander M. Klibanov, Biotechnology and Bioengineering, vol. XXX, pp. 31-36 (1987).
Sugar Polyether Polyols for Rigid Polyurethanes-Propoxylation of Disaccharides Under Alkaline Condition, Tito Viswanathan, Alan Toland and Rui-Qin Liu, Journal of Polymer Science: Part C: Polymer Letters, vol. 28, 95-100 (1990).
Novel Route to Chiral Polymers involving Biocatalytic Transesterification of O-Acryloyl Oximes, A Ghogare and G. Sudesh Kumar, J. Chem. Soc., Chem. Commun., 1990.
New Thermotropic Chiral Nematic Copolymers Using (1S,2S,3S,5R)-(+)-and (1R,2R,3R,5S)-(-)-Isopinocampheol as Building Blocks, S. H. Chen and M. L. Tsai, 1990 American Chemical Society.
Template Monomer Control of the Chirality Induction in the Polymer Backbone during Asymmetric Vinyl Polymerization, Gunter Wulff and Pradeep K. Dhal, Macromolecules 1990, 23, 4525-4527.
Polymerisation of Unsaturated Derivatives of 1,2:5,6-Di-O-isopropylidene-D-glucofuranose, W. A. P. Black, E. T. Dewar, and D. Rutherford, Arthur D. Little Research Institute, Inveresk Gate, Musselburgh, Midlothian.
"The Preparation of 4,6-Dichloro-4,6-Dideoxy-.alpha.-D-Galactopyranosyl 6-Chloro-6-Deoxy-.beta.-D-Fructofuranoside and the Conversion of Chlorinated Derivatives Into Anhydrides", Leslie Hough, Shashi P. Phadnis, and Edward Tarelli, Carbohydrate Research, 44 (1975) 37-44.
"C-Nuclear Magnetic Resonance (NMR) Spectra of O-Acylglucoses. Additivity of Shift Parameters and Its Application to Structure Elucidations", Kimihiro Yoshimoto, Yoshitaka Itatani, and Yoshisuke Tsuda, Chem. Pharm. Bull., 28(7)2065-2076 (1980).
"Selective tetratosylation of sucrose: isolation of the 2,6,1',6'-tetrasulphonate", John M. Ballard, Leslie Hough, Shashi P. Phadnis, and Anthony C. Richardson, Carbohydrate Research, 83 (1980) 138-141.
"The Selective Removal of Protecting Groups in Carbohydrate Chemistry", Alan H. Haines, Academic Press, Inc., 1981.
"Chemistry and New Uses of Sucrose: How Important?", Riaz Khan, Pure & Appl. Chem., vol. 56, No. 7, pp. 833-844, 1984.
"Ester Synthesis in Organic Solvent Catalyzed by Lipases Immobilized On Hydrophilic Supports", C. Marlot, G. Langrand, C. Triantaphylides and J. Baratti, Biotechnology Letters, vol. 7, No. 9, 647-650 (1985).
"Enzyme-catalyzed processes in organic solvents", Aleksey Zaks and Alexander M. Klibanov, Proc. Natl. Acad. Sci. USA, vol. 82, pp. 3192-3196, May 1985.
"Facile Enzymatic Preparation of Monoacylated Sugars in Pyridine", Michel Therisod and Alexander M. Klibanov, J. Am. Chem. Soc., vol. 108, No. 18, pp. 5638-5640, 1986.
"Enzymes that work in organic solvents", Alexander M. Klibanov, Chemtech, Jun. 1986.
"Lipase-Catalyzed Ester Exchange Reactions in Organic Media With Controlled Humidity", H. L. Goderis, G. Ampe, M. P. Feyten, B. L. Fouwe, W. M. Guffens, S. M. Van Cauwenbergh and P. P. Tobbach, Biotechnology and Bioengineering, vol. XXX, pp. 258-266 (1987).
"Quantitative Analyses of Biochemical Kinetic Resolution of Enantiomers. 2. Enzyme-Catalyzed Esterifications in Water-Organic Solvent Biphasic Systems", Ching-Shih Chen, Shih-Hsiung Wu, Gary Girdaukas, and Charles J. Sih, J. Am. Chem. Soc. 1987, 109, 2812-2817.
"Stereoselective Oligomerizations Catalyzed By Lipases In Organic Solvents", Alexey L. Margolin, Jean-Yves Crenne, and Alexander M. Klibanov, Tetrahedron Letters, vol. 28, No. 15, pp. 1607-1610, 1987.
"Regioselective Acylation of Secondary Hydroxyl Groups in Sugars Catalyzed by Lipases in Organic Solvents", Michel Therisod and Alexander M. Klibanov, J. Am. Chem. Soc. vol. 109, No. 13, pp. 3977-3981, 1987.
"Protease-Catalyzed Regioselective Esterification of Sugars and Related Compounds in Anhydrous Dimethylformamide", Serglo Riva, Joel Chopineau, A. P. G. Kieboom, and Alexander M. Klibanov, J. Am. Chem. Soc., vol. 110, No. 2, pp. 584-589, 1988.
"Enzymatic Synthesis of Macrocyclic Lactones", Guo Zhi-Wei and Charles J. Shih, J. Am. Chem. Soc., vol. 110, No. 6, pp. 1999-2001, 1988.
"Lipase-Catalysed Irreversible Transesterifications Using Enol Esters as Acylating Regents: Preparative Enantio- and Regioselective Syntheses of Alcohols, Glycerol Derivatives, Sugars, and Organometallics", Yi-Fong Wang, James J. Lalonde, Milagros Momongan, David E. Bergbreiter, and Chi-Huey Wong, J. Am. Chem. Soc., vol. 110, No. 21, pp. 7200-7205, 1988.
"Carbonates in Water-Restricted Environments", Daniel A. Abramowicz and Charles R. Keese, Biotechnology and Bioengineering, vol. 33, pp. 149-156 (1989).
"Biocatalytic Synthesis of Polymers. Synthesis of an Optically Active, Epoxy-Substituted Polyester by Lipase-Catalyzed Polymerization", J. Shield Wallace and Cary J. Morrow, Journal of Polymer Science: Part A: Chemistry, vol. 27, 2553-2567 (1989).
"Enzymatic catalysis in monophasic organic solvents", Jonathan S. Dordick, Enzyme Microb. Technol., 1989, vol. 11, Apr. 1989.
"Enzymatic catalysis in anhydrous organic solvents", Alexander M. Klibanov, Trends in Biochemical Science-Apr. 1989, vol. 14, No. 4.
"Enzymatic Synthesis of Various 1'-O-Sucrose and 1-O-Fructose Esters", Giacomo Carrea, Sergio Riva and Francesco Secundo, Chem. Soc. Perkin Trans I, 1989.
"Asymmetric Transformations Catalyzed by Enzymes in Organic Solvents", Alexander M. Klibanov, Acc. Chem. Res., vol. 23, No. 4, pp. 23, 114-120, 1990.

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