Biocatalyst-mediated selective acylation and deacylation chemistry on the secondary hydroxyl/amine groups of nucleosides

Abstract Nucleosides play a pivotal role in biological systems and therefore have attracted a lot of interest as chemotherapeutic agents in drug discovery. Over the years biocatalysts have emerged as a sustainable alternative to conventional synthetic catalysts. As a nature’s catalyst, they exhibit excellent selectivity, remarkable tolerance, and help in carrying out eco-friendly benign processes. The use of a biocatalyst as a regio- and enantioselective catalyst is particularly relevant in the transformations of nucleosides and their analogs because of the presence of multiple chiral centres. Herein, we discuss the recent advances in the Pseudomonas Cepacia Lipase mediated selective acylation and deacylation reactions of the secondary hydroxyl and amino groups of nucleosides and their analogs.

[1]  G. Miller,et al.  Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues , 2020, Molecules.

[2]  V. Kumar,et al.  Biocatalyst CAL-B catalyzed synthesis of modified nucleosides: An overview , 2019, Synthetic Communications.

[3]  Katherine L. Seley‐Radtke,et al.  The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold , 2018, Antiviral Research.

[4]  A. Najjar,et al.  Advanced Prodrug Strategies in Nucleoside and Non-Nucleoside Antiviral Agents: A Review of the Recent Five Years , 2017, Molecules.

[5]  R. Ebright,et al.  Antibacterial Nucleoside-Analog Inhibitor of Bacterial RNA Polymerase , 2017, Cell.

[6]  C. Britos,et al.  New developments in nucleoside analogues biosynthesis: A review , 2016 .

[7]  Guangdi Li,et al.  Approved Antiviral Drugs over the Past 50 Years , 2016, Clinical Microbiology Reviews.

[8]  M. Zong,et al.  The halo-substituent effect on Pseudomonas cepacia lipase-mediated regioselective acylation of nucleosides: A comparative investigation. , 2015, Journal of biotechnology.

[9]  H. Wagenknecht.  Nucleic acid chemistry , 2014, Beilstein journal of organic chemistry.

[10]  C. Olsen,et al.  Chemo-enzymatic synthesis of bicyclic 3′-azido- and 3′-amino-nucleosides , 2014 .

[11]  C. Olsen,et al.  Chemoenzymatic convergent synthesis of 2'-O,4'-C-methyleneribonucleosides. , 2014, The Journal of organic chemistry.

[12]  M. Zong,et al.  Influence of substituent groups in regioselective acylation of nucleosides by Novozym 435 lipase , 2013 .

[13]  Marion B. Ansorge-Schumacher,et al.  Immobilised lipases in the cosmetics industry. , 2013, Chemical Society reviews.

[14]  Fabien Zoulim,et al.  Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases , 2013, Nature Reviews Drug Discovery.

[15]  Maria Paola Costi,et al.  Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity , 2013, Scientific Reports.

[16]  M. Zong,et al.  Regioselective enzymatic procedure for preparing 3′-O-stearoyl-6-azauridine by using Burkholderia cepacia lipase , 2012, Biotechnology and Bioprocess Engineering.

[17]  Maigret Bernard,et al.  Combined docking and molecular dynamics simulations to enlighten the capacity of Pseudomonas cepacia and Candida antarctica lipases to catalyze quercetin acetylation. , 2011, Journal of biotechnology.

[18]  M. Zong,et al.  Highly Regioselective Synthesis of 3′-O-Acyl-Trifluridines Catalyzed by Pseudomonas cepacia Lipase , 2011, Applied biochemistry and biotechnology.

[19]  M. Zong,et al.  Regioselectivity-reversal in acylation of 6-azauridine catalyzed by Burkholderia cepacia lipase , 2011, Biotechnology Letters.

[20]  J. Polaina,et al.  Industrial Enzymes: Structure, Function and Applications , 2010 .

[21]  T. Tan,et al.  Biodiesel production with immobilized lipase: A review. , 2010, Biotechnology advances.

[22]  Ning Li,et al.  Biocatalytic transformation of nucleoside derivatives. , 2010, Biotechnology advances.

[23]  Ning Li,et al.  A simple procedure for the synthesis of potential 6-azauridine prodrugs by Thermomyces lanuginosus lipase , 2009 .

[24]  M. Zong,et al.  Recognition of acyl donors by lipase CAL‐B in the acylation of 6‐azauridine , 2009, Biotechnology progress.

[25]  M. Zong,et al.  Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition , 2009 .

[26]  M. Zong,et al.  Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition , 2008 .

[27]  H. Pellissier.  Recent Developments in Dynamic Kinetic Resolution , 2008 .

[28]  Ning Li,et al.  Enhancing the activity and regioselectivity of lipases for 3'-benzoylation of floxuridine and its analogs by using ionic liquid-containing systems. , 2008, Journal of biotechnology.

[29]  M. Zong,et al.  Regioselective synthesis of 3 '-O-caproyl-floxuridine catalyzed by Pseudomonas cepacia lipase , 2007 .

[30]  M. Zong,et al.  Novel and highly regioselective route for synthesis of 5-fluorouridine lipophilic ester derivatives by lipozyme TL IM. , 2007, Journal of biotechnology.

[31]  Y. Tor,et al.  Furan Decorated Nucleoside Analogues as Fluorescent Probes: synthesis, photophysical evaluation and site-specific incorporation. , 2007, Tetrahedron.

[32]  Y. Tor,et al.  Fluorescent pyrimidine ribonucleotide: synthesis, enzymatic incorporation, and utilization. , 2007, Journal of the American Chemical Society.

[33]  马丁,et al.  Regioselective synthesis of 3 -O-caproyl-floxuridine catalyzed by Pseudomonas cepacia lipase , 2007 .

[34]  Ramesh N. Patel.  Biocatalysis in the pharmaceutical and biotechnology industries , 2006 .

[35]  R. Kazlauskas,et al.  Remote Interactions Explain the Unusual Regioselectivity of Lipase from Pseudomonas cepacia toward the Secondary Hydroxyl of 2′‐Deoxynucleosides , 2006, Chembiochem : a European journal of chemical biology.

[36]  D. Seebach,et al.  Selective Acylations of Multifunctional Nucleophiles, Including Carbohydrates and Nucleosides, with Intermediates Generated by Wolff Rearrangement of Amino Acid Derived Diazo Ketones: Preparation of β‐Amino Acid Derivatives , 2006 .

[37]  E. De Clercq,et al.  Antiviral prodrugs – the development of successful prodrug strategies for antiviral chemotherapy , 2006, British journal of pharmacology.

[38]  I. Lavandera,et al.  Novel and efficient regioselective enzymatic approach to 3′-, 5′- and 3′,5′-di-O-crotonyl 2′-deoxynucleoside derivatives , 2005 .

[39]  E. De Clercq.  Recent highlights in the development of new antiviral drugs , 2005, Current Opinion in Microbiology.

[40]  Erik De Clercq,et al.  Antiviral drugs in current clinical use. , 2004 .

[41]  L. Cartee,et al.  Challenges in antimicrobial drug discovery and the potential of nucleoside antibiotics. , 2004, Current medicinal chemistry.

[42]  G. Peters,et al.  Antiproliferative activity and mechanism of action of fatty acid derivatives of arabinofuranosylcytosine in leukemia and solid tumor cell lines. , 2004, Biochemical pharmacology.

[43]  A. Matsuda,et al.  Antitumor activity of sugar‐modified cytosine nucleosides , 2004, Cancer science.

[44]  E. De Clercq,et al.  Synthesis, Protonation Behavior, Conformational Analysis, and Regioselective Enzymatic Acylation of the Novel Diamino Analogue of (E)-5-(2-Bromovinyl)-2′-deoxyuridine (BVDU) , 2003, Nucleosides, nucleotides & nucleic acids.

[45]  I. Lavandera,et al.  Novel and efficient syntheses of 3′,5′-diamino derivatives of 2′,3′,5′-trideoxycytidine and 2′,3′,5′-trideoxyadenosine. Protonation behavior of 3′,5′-diaminonucleosides , 2003 .

[46]  E. De Clercq,et al.  Synthesis and Antiviral Activity Assay of Novel (E)-3′,5′-Diamino-5-(2-bromovinyl)-2′,3′,5′-trideoxyuridine , 2003, Nucleosides, nucleotides & nucleic acids.

[47]  S. Fernández,et al.  Direct Regioselective Enzymatic Acylation of Nucleosides: Building-Blocks for the Solution Phase Synthesis of Oligonucleotides , 2003, Nucleosides, nucleotides & nucleic acids.

[48]  Natale Scaramozzino,et al.  Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses. , 2003, Antiviral research.

[49]  Andreas Schmid,et al.  The production of fine chemicals by biotransformations. , 2002, Current opinion in biotechnology.

[50]  Hye-Sook Kim,et al.  Mechanisms of cell death induced by 5-fluoro-2'-deoxyuridine (FUdR)--necrosis or apoptosis after treated with FUdR. , 2002, Nucleic acids research. Supplement.

[51]  S. Fernández,et al.  Building blocks for the solution phase synthesis of oligonucleotides: regioselective hydrolysis of 3',5'-Di-O-levulinylnucleosides using an enzymatic approach. , 2002, The Journal of organic chemistry.

[52]  I. Lavandera,et al.  First regioselective enzymatic acylation of amino groups applied to pyrimidine 3',5'-diaminonucleoside derivatives. Improved synthesis of pyrimidine 3',5'-diamino-2',3',5'-trideoxynucleosides. , 2001, The Journal of organic chemistry.

[53]  D. Richman.  Antiretroviral Activity of Emtricitabine, a Potent Nucleoside Reverse Transcriptase Inhibitor , 2000, Antiviral therapy.

[54]  V. Gotor,et al.  Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. , 2000, Chemical reviews.

[55]  E. Santaniello,et al.  The Action of Adenosine Deaminase (E.C. 3.5.4.4.) on Adenosine and Deoxyadenosine Acetates: The Crucial Role of the 5′-Hydroxy Group for the Enzyme Activity , 2000 .

[56]  E. Santaniello,et al.  Regioselective Hydrolysis of Diacetoxynaphthalenes Catalyzed by Pseudomonas sp. Lipase in an Organic Solvent , 2000 .

[57]  R. Kazlauskas,et al.  Molecular Basis for Enantioselectivity of Lipase from Pseudomonas cepacia toward Primary Alcohols. Modeling, Kinetics, and Chemical Modification of Tyr29 to Increase or Decrease Enantioselectivity. , 1999, The Journal of organic chemistry.

[58]  S. Fernández,et al.  Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides , 1998 .

[59]  J. Wengel,et al.  Enzyme-Mediated Protecting Group Chemistry on the Hydroxyl Groups of Nucleosides , 1996 .

[60]  L. Ling,et al.  Enzyme Aided Regioselective Acylation of Nucleosides , 1995 .

[61]  V. Gotor,et al.  Chemo-enzymatic synthesis of 2′-deoxynucleoside urethanes , 1993 .

[62]  V. Gotor,et al.  A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction , 1993 .

[63]  V. Gotor,et al.  Regioselective Acylation of 2′-Deoxynucleosides Through an Enzymatic Reaction with Oxime Esters , 1992 .

[64]  J. Double,et al.  Synthesis and cytotoxicity of shikimate analogues. Structure:activity studies based on 1-crotonyloxymethyl-3R,4R,5R-trihydroxycyclohex-2-enone. , 1992, Anti-cancer drug design.

[65]  K. Nozaki,et al.  Regioselective deprotection of 3′,5′-O-acylated pyrimidine nucleosides by lipase and esterase , 1989 .

[66]  P. Hodge,et al.  Protective groups in organic synthesis , 1981 .

[67]  C. Reese,et al.  Protection of alcoholic hydroxy groups as crotonate and related esters , 1977 .

[68]  J. G. Moffatt,et al.  Reactions of 2-acyloxyisobutyryl halides with nucleosides. 6. Synthesis and biological evaluation of some 3'-acyl derivatives of 2,2'-anhydro-1-(beta-D-arabinofuranosyl)cytosine hydrochloride. , 1976, Journal of Medicinal Chemistry.

[69]  J. G. Moffatt,et al.  Reactions of 2-acyloxyisobutyryl halides with nucleosides. 7. Synthesis and biological evaluation of some 2,2'-anhydro-1(3',5'-di-O-acyl-beta-D-arabinofuranosyl)cytosine hydrochlorides. , 1976, Journal of medicinal chemistry.

[70]  T. Takeuchi,et al.  The structure of a glyoxalase I inhibitor and its chemical reactivity with SH-compounds. , 1975, The Journal of antibiotics.

[71]  T. Takeuchi,et al.  A glyoxalase I inhibitor of a new structural type produced by Streptomyces. , 1975, The Journal of antibiotics.

[72]  H. Kaufman.  Clinical Cure of Herpes Simplex Keratitis by 5-Iodo-2'-Deoxyuridine , 1962, Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine.