CAS: 10300-22-8; (2R,3R,4S,5R)-2-(6-Amino-9H-Purin-9-yl)-5-(Hydroxymethyl)-4-Methoxytetrahydrofuran-3-Ol

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CAS号17287-03-5 三甲基氢氧化硫,甲醇溶液 | CAS号58-61-7 腺苷 | CAS号74-88-4 碘甲烷 | CAS号74230-06-1 trimethylseleno... | CAS号80-48-8 对甲苯磺酸甲酯 | CAS号1899-02-1 三甲基苯基氢氧化铵 | CAS号512-56-1 磷酸三甲酯 | CAS号18107-18-1 (三甲硅烷)重氮甲烷 | CAS号2140-79-6 2'-O-甲基腺苷 | CAS号60037-52-7 N6,O3'-methylad... | CAS号20649-46-1 2',3'-DIMETHOXY...

腺苷,碘甲烷置于sodium Hydride体系中,用 N,N-二甲基甲酰胺 用作溶剂,化学反应 4.0H,以27%的收率获得2'-O-甲基腺苷
参考文献:Synthesis And Conformational Analysis Of Phosphate-Methylated Rna Dinucleotides
标题:Synthesis And Conformational Analysis Of Phosphate-Methylated Rna Dinucleotides
摘要:Synthesis Of Rna Dimers Having A Methyl Phosphotriester Group As The Internucleoside Linkage Is Reported; Six Pairs Of Diasteroisomerically Pure Systems Were Prepared,I.E,R(Cpu) (15),R(Apu) (16),R(Cpc) (17),R(Apc) (18),R(Cpg) (19),And R(Apg) (20). Compounds 15-20 Are Stabilized By A 2'-O-Methyl Group In The 5'-Terminal Residue. The Present Systems Represent The Third Class Of Backbone-Modified Rna Oligomers,Following The 2'-O-Methylribonucleotide Phosphorothioates And The 2'-O-Methylribonucleotide Methyl Phosphonates. Our Synthetic Approach Comprises The Use Of 9-Fluorenylmethoxycarbonyl (Fmoc) Groups For Transient Protection Of The Exocyclic Nh2 Groups Of The Bases A,C,And G,Levulinoyl (Lev) Groups For The Transient Protection Of The 2'-And 3'-Oh Groups Of The 3'-Terminal Residues,Methanolic K2Co3 For The Simultaneous Removal Of Fmoc And Lev Groups With Full Preservation Of The Methyl Phosphotriester Function,And Finally Reversed-Phase HPLC Separation Of The S(P) And R(P) Diastereoisomers. The Availability Of The Six Dimers In Diastereoisomerically Pure Form Enabled Us To Examine The Molecular Conformations Using High-Field NMR And Circular Dichroism (Cd) Spectroscopy. These Studies Led To The Following Conclusions: (I) NMR J-Coupling Analysis: The Central C4'-C5' (Gamma) And C5'-O5' (Beta) Bonds In 15-20 Show Less Preference For The Gamma+ And Beta-T Rotamers,In Comparison With Their Natural Analogues,I.E.,Base Stacking Is Diminished Upon Introduction Of The Two Methyl Groups On O2' And On The Phosphate Methyl Groups On O2' And On The Phosphate Group; (II) Cd Analysis: 15-20 Show Substantially Reduced Molecular Ellipticities When Compared To The Natural Counterparts,Which Also Reveals That Base Stacking Is Reduced; (III) Uv And Variable-Temperature H-1 NMR Measurements: (S(P)-And (R(P))-19 Show Self-Association,Via The Formation Of A Right-Handed Miniduplex With Two C-G Base Pairs ((S(P)-19,T(M) = 9.3-Degrees-C,Concn = 36.6-Mu-M; (R(P))-19,T(M) = 8.7-Degrees-C,Concn = 48.1-Mu-M). The Present Conformational Data On (R(P))-And (S(P))-15-20 Are In Agreement With Literature Data On Other Phosphate-Triesterified Oligonucleotides,E.G.,The Trimer D(T(Poet)G(Poet)G) And The Tetramer D(T(Poet)T(Poet)C(Poet)A). While The Latter Systems Also Showed Little Base-Base Stacking,It Was Established That They Readily Form A Local Duplex With A Complementary Natural Rna Sequence. Hence We Anticipate That Phosphate-Methylated 2'-O-Methyl-Rna Oligomers,Longer Than The Dimer Systems Described In The Present Work,Will Also Hybridize Easily With Complementary Natural Rna.
Doi:10.1021/jo00020A028

专利信息

专利号:US-2004054162-A1
优先权日:2001-10-30
标 题:Molecular detection systems utilizing reiterative oligonucleotide synthesis
发明人：HANNA MICHELLE M
摘要:The present invention provides methods for detecting the presence of a target molecule by the use of nucleotide analogs containing moieties that enable detection. Such analogs may be incorporated into nucleic acids. In one embodiment, nucleotide analogs are used in a process generating multiple detectable oligonucleotides through reiterative enzymatic oligonucleotide synthesis events on a defined polynucleotide sequence. The methods generally comprise using a nucleoside, a mononucleotide, an oligonucleotide, or a polynucleotide, or analog thereof, to initiate synthesis of an oligonucleotide product that is substantially complementary to a target site on the defined polynucleotide sequence; optionally using nucleotides or nucleotide analogs as oligonucleotide chain elongators or chain terminators to terminate the polymerization reaction; and detecting multiple oligonucleotide products that have been synthesized by the polymerase.