LEADER 10533nam 2200505 450 001 9910555166603321 005 20210901203039.0 010 $a3-527-81207-5 010 $a3-527-81209-1 010 $a3-527-81210-5 035 $a(CKB)4100000007111273 035 $a(MiAaPQ)EBC5568547 035 $a(Au-PeEL)EBL5568547 035 $a(OCoLC)1061105639 035 $a(iGPub)WILEYB0037091 035 $a(EXLCZ)994100000007111273 100 $a20181122d2019 uy 0 101 0 $aeng 135 $aurcnu|||||||| 181 $ctxt$2rdacontent 182 $cc$2rdamedia 183 $acr$2rdacarrier 200 00$aEnzymatic and chemical synthesis of nucleic acid derivatives /$fedited by Jesus Fernandez-Lucas, Maria-Jose Camarasa Rius 205 $a1st ed. 210 1$aWienhem, Germany :$cWiley-VCH Verlag,$d2019. 215 $a1 online resource (351 pages) 311 $a3-527-34376-8 327 $aCover -- Title Page -- Copyright -- Contents -- Preface -- Chapter 1 Enzymatic Synthesis of Nucleoside Analogues by Nucleoside Phosphorylases -- 1.1 Introduction -- 1.1.1 Nucleosides and Nucleoside Analogues -- 1.1.2 Enzymes Involved in the Enzymatic Synthesis of Nucleoside Analogues -- 1.2 Nucleoside Phosphorylases -- 1.2.1 Classification and Substrate Spectra of Nucleoside Phosphorylases -- 1.2.1.1 Nucleoside Phosphorylase?I Family -- 1.2.1.2 Nucleoside Phosphorylase?II Family -- 1.2.2 Limitations in the Current Classification -- 1.2.3 Reaction Mechanism -- 1.2.4 Domain Structure and Active Site Residues of Nucleoside Phosphorylases -- 1.2.4.1 NP?I Family Members -- 1.2.4.2 NP?II Family Members -- 1.3 Enzymatic Approaches to Produce Nucleoside Analogues Using Nucleoside Phosphorylases -- 1.3.1 One?pot Two?Step Transglycosylation Reaction -- 1.3.2 Pentofuranose?1?phosphate as Universal Glycosylating Substrate for Nucleoside Phosphorylase (NP) -- 1.3.2.1 Nucleoside Synthesis from Chemically Synthesized Pentose?1P -- 1.3.2.2 Nucleosides Synthesis from d?Glyceraldehyde?3?phosphate -- 1.3.2.3 Nucleoside Synthesis from d?Pentose -- 1.3.2.4 Nucleoside Synthesis from Enzymatically Produced Pentose?1P -- 1.4 Approaches to Produce Nucleoside Analogues -- 1.4.1 Whole Cell Catalysis -- 1.4.2 Crude Enzyme Extract -- 1.4.3 Application of Purified Enzymes -- 1.4.3.1 Immobilized Enzymes -- 1.4.3.2 Enzyme Reactors -- 1.5 Upscaling Approaches for the Production of Nucleoside Analogues -- 1.6 Production of Pharmaceutically Active Compounds by Nucleoside Phosphorylases -- 1.7 Outlook for the Application of Nucleoside Phosphorylase in the Production of Nucleoside Analogues -- References -- Chapter 2 Enzymatic Phosphorylation of Nucleosides -- 2.1 Introduction -- 2.2 Nonspecific Acid Phosphatases (NSAPs) -- 2.3 Deoxyribonucleoside Kinases (dNKs) -- 2.4 Conclusion. 327 $aReferences -- Chapter 3 Enzymatic Synthesis of Nucleic Acid Derivatives Using Whole Cells -- 3.1 Introduction -- 3.2 Nucleoside Synthesis Mediated by Microbial Nucleoside Phosphorylases -- 3.3 Nucleoside Analogues Synthesis by the Combined Action of Microbial Nucleoside Phosphorylases and Other Enzymes -- 3.3.1 Nucleoside Phosphorylases Coupled to Deaminases -- 3.3.2 Nucleoside Phosphorylases Coupled to Phosphopentomutase -- 3.3.3 Nucleoside Phosphorylases Coupled to Phosphopentomutase and Other Enzymes -- 3.3.4 Nucleoside Phosphorylases Coupled to Other Enzymes -- 3.4 Chemoenzymatic Preparation of Nonconventional Nucleoside Analogues Involving Whole Cell Biocatalyzed Key Steps -- 3.4.1 l?Nucleosides -- 3.4.2 Carbocyclic Nucleosides -- 3.4.3 C?Nucleosides -- 3.5 Nucleoside Prodrugs Preparation by Whole Cell Systems -- 3.5.1 Acylnucleosides -- 3.5.2 Nucleoside Phosphates -- 3.6 Other Nucleoside Derivatives -- 3.6.1 NDP -- 3.6.2 NDP?sugar -- 3.7 Perspectives -- References -- Chapter 4 Enzymatic Synthesis of Nucleic Acid Derivatives by Immobilized Cells -- 4.1 Introduction -- 4.2 Nucleic Acid Derivatives -- 4.3 Whole Cell Immobilization: Generalities -- 4.4 Synthesis of Nucleosides by Immobilized Cells -- 4.4.1 Natural Nucleoside Synthesis -- 4.4.2 Nucleoside Analogues Synthesis -- 4.4.3 Nucleoside Analogues Derivatives Synthesis -- 4.5 Conclusion -- References -- Chapter 5 Enzymatic Synthesis of Nucleic Acid Derivatives by Immobilized Enzymes -- 5.1 Introduction -- 5.2 Immobilized Glycosyltransferases -- 5.2.1 Immobilized Nucleoside Phosphorylases -- 5.2.1.1 Stabilization of Nucleoside Phosphorylases by Immobilization -- 5.2.1.2 Synthesis of Nucleosides Catalyzed by Immobilized Nucleoside Phosphorylases -- 5.2.2 Immobilized Nucleoside 2'?Deoxyribosyltransferases -- 5.2.2.1 Stabilization of Nucleoside 2'?Deoxyribosyltransferases by Immobilization. 327 $a5.2.2.2 Synthesis of Nucleosides Catalyzed by Immobilized 2'?Deoxyribosyltransferases -- 5.2.3 Immobilized Nucleobase Phosphoribosyltransferases -- 5.3 Immobilized Nucleoside Oxidase -- 5.4 Immobilized Hydrolases -- 5.4.1 Immobilized Lipases -- 5.4.2 Immobilized Proteases -- 5.4.3 Immobilized Esterases -- 5.4.4 Immobilized Deaminases -- 5.4.5 Immobilized S?Adenosylhomocysteine Hydrolases -- 5.5 Immobilized Phosphopentomutases -- 5.6 Immobilized Deoxyribonucleoside Kinases -- References -- Chapter 6 Synthesis of Nucleic Acid Derivatives by Multi?Enzymatic Systems -- 6.1 Multi?Enzymatic Systems in Biosynthesis -- 6.2 General Overview of Multi?Enzymatic Synthesis of Nucleic Acid Derivatives -- 6.3 Multi?Enzymatic Synthesis of Nucleosides and Their Derivatives -- 6.3.1 Multi?Enzymatic Synthesis of Nucleosides and Their Analogues by Nucleoside Phosphorylase -- 6.3.2 Transglycosylation Coupled with Xanthine Oxidase -- 6.3.3 Transglycosylation Reactions Coupled with Deamination -- 6.3.4 ADase in Combination with Lipase -- 6.3.5 Esterification of Nucleosides -- 6.3.6 Multi?Enzymatic Synthesis of Fluorine Nucleosides -- 6.3.7 Multi?Enzymatic Synthesis of Nucleosides via R5P -- 6.3.8 Other Reactions -- 6.4 Multi?Enzymatic Synthesis of Nucleotides and Their Derivatives -- 6.4.1 Multi?Enzymatic Synthesis of NMPs and dNMPs -- 6.4.2 Multi?Enzymatic Synthesis of NTPs and dNTPs -- 6.4.3 Multi?Enzymatic Synthesis of NDP?Sugars and Other NDP Derivatives -- 6.5 Conclusion -- References -- Chapter 7 Enzymatic Synthesis Using Polymerases of Modified Nucleic Acids and Genes -- 7.1 Introduction -- 7.2 Types of XNA Biomolecules -- 7.3 Enzymatic Synthesis of XNA and DNA Polymerases -- 7.4 Base?Modified XNAs (Base?XNAs) -- 7.4.1 Nucleobase Analogues -- 7.4.1.1 Non?Canonical Nucleotides -- 7.4.1.2 Amino?acid?Like Groups -- 7.4.1.3 Functional Tags -- 7.4.2 Unnatural Base Pairs. 327 $a7.4.2.1 Hydrogen?Bonding Base Pairs -- 7.4.2.2 Hydrophobic Base Pairs -- 7.5 Sugar?Modified XNAs (Sugar?XNAs) -- 7.5.1 Pentose?XNA -- 7.5.2 2'?Ribose?XNA -- 7.6 Phosphodiester Backbone?XNA -- 7.7 A Mirror?Image l?DNA -- 7.8 Conclusions -- References -- Chapter 8 Synthetic Approaches to the Fleximer Class of Nucleosides - A Historic Perspective -- 8.1 Distal Fleximers -- 8.1.1 Ribose Distal Fleximers -- 8.1.2 2'?Deoxyribose Distal Fleximers -- 8.1.3 2'?Modified Distal Fleximers -- 8.2 Proximal Fleximers -- 8.2.1 Ribose Proximal Fleximers -- 8.2.2 2'?Deoxyribose Proximal Fleximers -- 8.2.3 Carbocyclic Proximal Fleximers -- 8.2.4 Proximal Fleximers from Other Groups -- 8.3 "Reverse" Fleximers -- 8.4 Acyclic Fleximers -- 8.5 Conclusion -- References -- Chapter 9 Synthesis of Oligonucleotides Carrying Nucleic Acid Derivatives of Biomedical and Structural Interest -- 9.1 Introduction -- 9.2 Oligonucleotides Carrying the DNA Lesion O6?Alkylguanine -- 9.3 The Effect of Chemical Modifications in Non?Canonical DNA Structures -- 9.3.1 Triplex?Forming Oligonucleotides -- 9.3.2 G?quadruplex?Forming Oligonucleotides -- 9.3.3 Oligonucleotides Forming i?Motif Structures -- 9.4 Modified siRNAs for Gene Silencing -- 9.4.1 Modifications of the 3'?Overhangs -- 9.4.2 Modifications of the 5'?End -- References -- Chapter 10 Synthesis of Carbohydrate-Oligonucleotide Conjugates and Their Applications -- 10.1 Introduction -- 10.2 Synthesis of COCs -- 10.2.1 On?Support Synthesis -- 10.2.1.1 Phosphoramidite Chemistry -- 10.2.1.2 Derivatization of Nucleoside Base Residues -- 10.2.1.3 Oximation Chemistry -- 10.2.1.4 Amide Chemistry -- 10.2.1.5 Urea Chemistry -- 10.2.1.6 CuAAC Chemistry -- 10.2.2 Solution?Phase Conjugation -- 10.2.2.1 Disulfide Formation -- 10.2.2.2 Nucleophilic Addition on Unsaturated Carbon -- 10.2.2.3 Carbonyl Addition-Elimination Reaction. 327 $a10.2.2.4 CuAAC Chemistry -- 10.2.2.5 Diazocoupling Reaction -- 10.2.2.6 Amide Bond Formation -- 10.2.2.7 Enzymatic Incorporation of Saccharides or Nucleotides -- 10.3 Synthesis of Glycocluster Oligonucleotides -- 10.3.1 dsDNA Scaffolds -- 10.3.2 Non?Canonical DNA Scaffolds (G4 and three?Way Junction) -- 10.3.3 Organic Spacer Scaffolds -- 10.3.4 Biomolecules as Scaffolds -- 10.4 Applications of COCs -- 10.4.1 Improving Cellular Uptake -- 10.4.2 Molecular Interactions Probes -- 10.4.3 Lectin Binding and Glycoarrays -- 10.5 Outlook -- References -- Chapter 11 Advances in Light?Directed Synthesis of High?Density Microarrays and Extension to RNA and 2'F?ANA Chemistries -- 11.1 Introduction -- 11.2 Phosphoramidite Chemistry Applied to the Photolithographic Synthesis of Microarrays -- 11.3 Recent Improvements in the Synthesis of DNA Microarrays -- 11.4 Synthesis of RNA Microarrays -- 11.5 Enzymatic Approaches to RNA Array Synthesis -- 11.6 Synthesis of 2'F?ANA Microarrays -- 11.7 Conclusion and Outlook -- References -- Chapter 12 SAMHD1?Mediated Negative Regulation of Cellular dNTP Levels: HIV?1, Innate Immunity, and Cancers -- 12.1 Cellular dNTP Concentrations -- 12.2 SAMHD1 and Negative Regulation of Cellular dNTPs -- 12.3 SAMHD1 Substrates, Activators, and Inhibitors -- 12.4 SAMHD1 and HIV?1 Reverse Transcription -- 12.5 SAMHD1 Mutations and Innate Immunity -- 12.6 SAMHD1 and Cancers -- 12.7 Summary -- Acknowledgment -- References -- Index -- EULA. 606 $aNucleic acids$xSynthesis 608 $aElectronic books. 615 0$aNucleic acids$xSynthesis. 676 $a574.8732 702 $aFernandez-Lucas$b Jesus 702 $aCamarasa Rius$b Maria-Jose 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910555166603321 996 $aEnzymatic and chemical synthesis of nucleic acid derivatives$92817070 997 $aUNINA