Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution.

The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.

[1]  O. Ramström,et al.  Dynamic asymmetric hemithioacetal transformation by lipase-catalyzed γ-lactonization: in situ tandem formation of 1,3-oxathiolan-5-one derivatives. , 2012, Chemistry.

[2]  J. Bäckvall,et al.  Enantioselective synthesis of α-methyl carboxylic acids from readily available starting materials via chemoenzymatic dynamic kinetic resolution. , 2010, Journal of Organic Chemistry.

[3]  P. Merino,et al.  Chemical synthesis of heterocyclic-sugar nucleoside analogues. , 2010, Chemical reviews.

[4]  Olof Ramström,et al.  Direct STD NMR identification of beta-galactosidase inhibitors from a virtual dynamic hemithioacetal system. , 2010, Angewandte Chemie.

[5]  O. Ramström,et al.  Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides , 2010 .

[6]  O. Ramström,et al.  Dynamic asymmetric multicomponent resolution: lipase-mediated amidation of a double dynamic covalent system. , 2009, Journal of the American Chemical Society.

[7]  G. Singh,et al.  A Novel Method for Large-Scale Synthesis of Lamivudine through Cocrystal Formation of Racemic Lamivudine with (S)-(−)-1,1′-Bi(2-naphthol) [(S)-(BINOL)] , 2009 .

[8]  R. Larsson,et al.  Direct Asymmetric Dynamic Kinetic Resolution by Combined Lipase Catalysis and Nitroaldol (Henry) Reaction , 2008 .

[9]  R. Larsson,et al.  Dynamic combinatorial resolution: direct asymmetric lipase-mediated screening of a dynamic nitroaldol library. , 2007, Angewandte Chemie.

[10]  B. Martín‐Matute,et al.  (S)-selective kinetic resolution and chemoenzymatic dynamic kinetic resolution of secondary alcohols. , 2006, Chemistry.

[11]  A. J. Whitehead,et al.  Practical enantioselective synthesis of lamivudine (3TC™) via a dynamic kinetic resolution , 2005 .

[12]  刘金明,et al.  IL-13受体α2降低血吸虫病肉芽肿的炎症反应并延长宿主存活时间[英]/Mentink-Kane MM,Cheever AW，Thompson RW，et al//Proc Natl Acad Sci U S A , 2005 .

[13]  A. Kademi,et al.  Lipases and their industrial applications , 2004, Applied biochemistry and biotechnology.

[14]  Bernhard Hauer,et al.  Industrial methods for the production of optically active intermediates. , 2004, Angewandte Chemie.

[15]  Daeho Kim,et al.  (S)-selective dynamic kinetic resolution of secondary alcohols by the combination of subtilisin and an aminocyclopentadienylruthenium complex as the catalysts. , 2003, Journal of the American Chemical Society.

[16]  H. Schoemaker,et al.  Dispelling the Myths--Biocatalysis in Industrial Synthesis , 2003, Science.

[17]  M. Ikunaka.  A process in need is a process indeed: scalable enantioselective synthesis of chiral compounds for the pharmaceutical industry. , 2003, Chemistry.

[18]  Manfred T Reetz,et al.  New methods for the high-throughput screening of enantioselective catalysts and biocatalysts. , 2002, Angewandte Chemie.

[19]  Ji-zhen Li,et al.  THE CHEMICAL RESOLUTION OF RACEMIC CIS-2-HYDROXYMETHYL-5-(CYTOSINE-1′-YL)-1,3-OXATHIOLANE (BCH-189)—ONE DIRECT METHOD TO OBTAIN LAMIVUDINE AS ANTI-HIV AND ANTI-HBV AGENT , 2002 .

[20]  R. Kazlauskas,et al.  A structure-based rationalization of the enantiopreference of subtilisin toward secondary alcohols and isosteric primary amines , 1997 .

[21]  C. Rayner,et al.  ENANTIOSELECTIVE ENZYMATIC SYNTHESIS OF THE ANTI-VIRAL AGENT LAMIVUDINE (3TC) , 1995 .

[22]  P. Ravenscroft,et al.  Diastereoselective Synthesis of the Potent Antiviral Agent (-)-2'-Deoxy-3'-thiacytidine and Its Enantiomer , 1995 .

[23]  R. Cousins,et al.  Enzymic resolution of oxathiolane intermediates — an alternative approach to the anti-viral agent lamivudine (3TC™) , 1995 .

[24]  R. Schinazi,et al.  Asymmetric synthesis and biological evaluation of beta-L-(2R,5S)- and alpha-L-(2R,5R)-1,3-oxathiolane-pyrimidine and -purine nucleosides as potential anti-HIV agents. , 1993, Journal of medicinal chemistry.

[25]  R. Schinazi,et al.  Enzyme-mediated enantioselective preparation of pure enantiomers of the antiviral agent 2',3'-dideoxy-5-fluoro-3'-thiacytidine (FTC) and related compounds , 1992 .

[26]  R. Schinazi,et al.  Deoxycytidine deaminase-resistant stereoisomer is the active form of (+/-)-2',3'-dideoxy-3'-thiacytidine in the inhibition of hepatitis B virus replication. , 1992, The Journal of biological chemistry.

[27]  J. Cameron,et al.  (-)-2'-deoxy-3'-thiacytidine is a potent, highly selective inhibitor of human immunodeficiency virus type 1 and type 2 replication in vitro , 1992, Antimicrobial Agents and Chemotherapy.

[28]  R. Schinazi,et al.  Synthesis of enantiomerically pure (2'R,5'S)-(-)-1-(2-hydroxymethyloxathiolan-5-yl)cytosine as a potent antiviral agent against hepatitis B virus (HBV) and human immunodeficiency virus (HIV) , 1992 .

[29]  R. Schinazi,et al.  In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of oxathiolanyl and dioxolanyl nucleoside analogues , 1991 .

[30]  R. Schinazi,et al.  Inhibition of the replication of hepatitis B virus in vitro by 2',3'-dideoxy-3'-thiacytidine and related analogues. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[31]  Aviva Rappaport,et al.  A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa , 1991 .

[32]  O. Ramström,et al.  In situ evaluation of lipase performances through dynamic asymmetric cyanohydrin resolution. , 2011, Organic & biomolecular chemistry.

[33]  R. Larsson,et al.  Dynamic Combinatorial Thiolester Libraries for EfficientCatalytic Self‐Screening of Hydrolase Substrates , 2006 .

[34]  Ole Kirk,et al.  One Biocatalyst–Many Applications: The Use of Candida Antarctica B-Lipase in Organic Synthesis , 1998 .

[35]  Alexander D. Garnovskii,et al.  Organic Reactions , 1966, Nature.