Non-homogeneous systems for the resolution of enantiomeric...

Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...

Reexamination Certificate

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C435S118000, C435S135000

Reexamination Certificate

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07659106

ABSTRACT:
The present invention relates to a process for the biocatalyst-mediated enantioselective conversion of enantiomeric mixtures of hydrophobic esters using a biphasic solvent system. More particularly, the present invention relates to the enzyme-mediated enantioselective synthesis of anti-viral compounds, such as 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane (FTC) and its analogues, in a non-homogenous reaction system.

REFERENCES:
patent: 4800162 (1989-01-01), Matson
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5047407 (1991-09-01), Belleau et al.
patent: 5057427 (1991-10-01), Wald et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5248776 (1993-09-01), Chu et al.
patent: 5276151 (1994-01-01), Liotta
patent: 5466806 (1995-11-01), Belleau et al.
patent: 5486520 (1996-01-01), Belleau et al.
patent: 5538975 (1996-07-01), Dionne
patent: 5539116 (1996-07-01), Liotta et al.
patent: 5587480 (1996-12-01), Belleau et al.
patent: 5618820 (1997-04-01), Dionne
patent: 5663320 (1997-09-01), Mansour et al.
patent: 5684164 (1997-11-01), Belleau et al.
patent: 5693787 (1997-12-01), Mansour et al.
patent: 5696254 (1997-12-01), Mansour et al.
patent: 5700937 (1997-12-01), Liotta et al.
patent: 5728575 (1998-03-01), Liotta et al.
patent: 5744596 (1998-04-01), Mansour et al.
patent: 5756706 (1998-05-01), Mansour et al.
patent: 5763606 (1998-06-01), Mansour et al.
patent: 5814639 (1998-09-01), Liotta et al.
patent: 5827727 (1998-10-01), Liotta et al.
patent: 5892025 (1999-04-01), Liotta et al.
patent: 5914331 (1999-06-01), Liotta et al.
patent: 5914400 (1999-06-01), Liotta et al.
patent: 5922867 (1999-07-01), Mansour et al.
patent: 6979561 (2005-12-01), Almond et al.
patent: 0 337 713 (1989-10-01), None
patent: 0 382 526 (1990-08-01), None
patent: 0 515 144 (1992-11-01), None
patent: 0 515 156 (1992-11-01), None
patent: 0 526 253 (1993-02-01), None
patent: 0 711 771 (1996-05-01), None
patent: 0 513 200 (1998-09-01), None
patent: 0 872 237 (1998-10-01), None
patent: 08092269 (1996-04-01), None
patent: WO 91/11186 (1991-08-01), None
patent: WO 91/17159 (1991-11-01), None
patent: WO 92/02617 (1992-02-01), None
patent: WO 92/14743 (1992-09-01), None
patent: WO 92/15308 (1992-09-01), None
patent: WO 92/15309 (1992-09-01), None
patent: WO 92/18517 (1992-10-01), None
patent: WO 94/09793 (1994-05-01), None
patent: WO 96/30369 (1996-10-01), None
patent: WO 97/44445 (1997-11-01), None
patent: WO 98/46732 (1998-10-01), None
patent: WO 00/22157 (2000-04-01), None
Ariente-Fliche et al., “How to Synthesize Easily Dimethyl (2R) and (2S)-Formylcyclopropane-1,1-Dicarboxylate, a Precursor of a Wide Variety of Substituted Aminocyclopropanecarboxilic Acids,”Synth. Commun., 22(8):1149-1153 (1992).
Basavaiah et al., “Enantioselective Synthesis of (1R,2R)- and (1S,2S)-2-Nitroxycyclohexan-l-ols,” Tetrahedron:Asymmetry, 7(1):13-16 (1996,).
Basavaiah et al., “Enantioselective synthesis using crude enzymes,”Pure and Appl. Chem., 64(8):1067-1072 (1992).
Belleau, et al., “Oxidative Degradation of L-Ascorbic Acid Acetals to 2′,3′-Dideoxy-3′-Oxaribofuranoside. Synthesis of Enantiomerically Pure 2′,3′-Dideoxy-3′-Oxacytidine Stereoisomers as Potential Antiviral Agents,”Tet. Lett., 33(46):6949-6952 (1992).
Brand, S., et al., “New enantioselective routes to cyclic and acyclic S,O-acetals; enzymic resolution of .alpha.-acetoxysulfides:and enantiolselective synthesis of the antiviral agent Lamivudine,”Phosphorus, Sulfur, and Silicon and the Related Elements, vol. 120-121, pp. 367-368 (1997).
Choi, W.-B., et al., “In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of oxathiolanyl and dioxolanyl nucleoside analogues,”J. Am. Chem. Soc., 113(24):9377-9379 (1991).
Davies et al., “Biotransformations in Preparative Organic Chemistry. The Use of Isolated Enzymes and Whole Cell Systems in Synthesis,” Academic Press: London, 1989, pp. 10, 25, 37, 43, 50, 76.
Drauz, K., and Waldmann, H.,Enzyme Catalysis in Organic Synthesis, vol. 1, (VCH, Weinheim, Germany, 1995), pp. 23, 201, 202.
Du et al., “Asymmetric Synthesis of Oxazolidine Nucleosides and Related Chemistry,”Nucleosides and Nucleotides, 17(1-3):1-13 (1998).
Hoong,L.K., et al, “Enzyme-Mediated Enantioselective Preparation of Pure Enantiomers of the Antiviral Agent 2′,3′-Dideoxy-5-fluoro-3′-thiacytidine (FTC) and Related Compounds,”J. Org. Chem., 57:5563-5565 (1992).
Hultin et al., “Dilemma Regarding an Active Site Model for Porcine Pancreatic Lipase,”Tetrahedron Letters, 33(11):1399-1402 (1992).
Jones, “Enzymes in Organic Synthesis,”Tetrahedron, 42(13):3351-3403 (1986).
Jones, “Probing the specificity of synthetically useful enzymes,”Can. J. Chem., 71:1273-1282 (1993).
Kraus et al., “Synthesis of New 2,5-Substituted 1,3-Oxathiolanes. Intermediates in Nucleoside Chemistry,”Synthesis, Nov. 1991:1046-1048.
Lalonde et al., “Cross-Linked Crystals ofCandida rugosaLipase: Highly Efficient Catalysts for the Resolution of Chiral Esters,”J. Am. Chem. Soc., 117(26):6845-6852 (1995).
Mahmoudian et al., “Resolution of 4-amino-cyclopentanecarboxylic acid methyl esters using hydrolytic enzymes,”Enzyme and Microbial Technology, 14:911-916 (1992).
McIntosh et al., “2 Mercaptoaldehyde dimers and 2,5-dihydrothiophenes from 1,3-oxathiolan-5-ones,”Can. J. Chem., 61:1872-1875 (1983).
Milton et al., “Enzymatic Resolution of .alpha.-Acetoxysulfides: A New Approach to the Synthesis of Homochiral S,O-Acetals,”Tetrahedron: Asymmetry, 6(8):1903-1906 (1995).
Norbeck, D. W. et al., “A new 2′,3′-dideoxynucleoside prototype with in vitro activity against HIV,”Tetrahedron Letters, 30(46):6263-6266 (1989).
Ohno et al., “Chiral Synthons by Ester Hydrolysis Catalyzed by Pig Liver Esterase,”Organic Reactions, 37:1-55 (1989).
Provencher et al., “A Concluding Specification of the Dimensions of the Active Site Model of Pig Liver Esterase,”J. Org. Chem., 59:2729-2732 (1994).
Provencher et al., “Enzymes in Organic Synthesis 51. Probing the Dimensions of the Large Hydrophobic Pocket of the Active Site of Pig Liver Esterase,”Tetrahedron: Asymmetry, 4(9):2025-2040 (1993).
Ross, A.C., et al., “Organic solvent functional group effect on enzyme inactivation by the interfactial mechanism,”J. Molec. Catalysis B. Enzymatic, 8:183-192 (2000).
Schinazi et al., “Selective Inhibition of Human Immunodeficiency Viruses by Racemates and Enantiomers of cis-5-Fluoro-1-[2-(Hydroxymethyl)-1,3-Oxathiolan-5-yl]Cytosine,” Antimicrobial Agents and Chemotherapy, 36(11):2423-2431 (1992).
Sih et al., “Resolution of Enantiomers via Biocatalysis,”Topics in Stereochemistry, 1989:63-125.
Toone et al., “Active-Site Model for Interpreting and Predicting the Specificity of Pig Liver Esterase,”J. Am. Chem. Soc., 112:4946-4952 (1990).
Toone et al., “Enzymes in Organic Synthesis 49. Resolution of Racemic Monocyclic Esters with Pig Liver Esterase,”Tetrahedron: Asymmetry, 2(3):207-222 (1991).
Toone et al., “Enzymes in Organic Synthesis 50. Probing the Dimensions of the Large Hydrophobic Binding Region of the Active Site of Pig Liver Esterase Using Substituted Aryl Malonate Substrates,”Tetrahedron: Asymmetry, 2(10):1041-1052 (1991).
Whitesides et al., “Enzymes as Catalyst in Synthetic Organic Chemistry,”Angew. Chem. Int. Ed. Eng., 24(8):617-653 (1985).

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