Literature DB >> 1005124

Nucleoside-3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. III. An improved preparation of nucleoside 3'-phosphotriesters, their 1H NMR characterization and new conditions for removal of 2-cyanoethyl group.

R W Adamiak, M Z Barciszewska, E Biala, K Grzéskowiak, R Kierzek, A Kraszewski, W T Markiewicz, M Wiewiórowski.   

Abstract

An improved procedure for the transformation of 5'-O-monomethoxytrityl-2'-O-acetyl-3'-phosphates of uridine la, inosine ib and 6-N-benzoyladenosine lc into corresponding 3'/2,2,2-trichloroethyl, 2-cyanoethyl/-phosphates iiaic is reported. H NMR characterization of nucleoside 3'-phosphotriesters is presented. New conditions i.e. anhydrous triethylamine-pyridine treatment have been found for the selective removal of 2-cyanoethyl group from nucleoside 3'-phosphotriesters in the presence of neighbouring 2'-O-acetyl one.

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Year:  1976        PMID： 1005124      PMCID： PMC343184          DOI： 10.1093/nar/3.12.3397

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  3 in total

1.  Improved triester approach for the synthesis of pentadecathymidylic acid.

Authors:  K Itakura; N Katagiri; C P Bahl; R H Wightman; S A Narang
Journal:  J Am Chem Soc       Date:  1975-12-10       Impact factor: 15.419

2.  Deoxy oligonucleotide synthesis via the triester method.

Authors:  J C Catlin; F Cramer
Journal:  J Org Chem       Date:  1973-01-26       Impact factor: 4.354

3.  Studies on polynucleotides. LI. Syntheses of the 64 possible ribotrinucleotides derived from the four major ribomononucleotides.

Authors:  R Lohrmann; D Söll; H Hayatsu; E Ohtsuka; H G Khorana
Journal:  J Am Chem Soc       Date:  1966-02-20       Impact factor: 15.419
  3 in total
  10 in total

1.  Chemical synthesis of branched RNA.

Authors:  R Kierzek; D W Kopp; M Edmonds; M H Caruthers
Journal:  Nucleic Acids Res       Date:  1986-06-25       Impact factor: 16.971

2.  A rapid and convenient synthesis of poly-thymidylic acid by the modified triester approach.

Authors:  A K Sood; S A Narang
Journal:  Nucleic Acids Res       Date:  1977-08       Impact factor: 16.971

3.  Nucleoside 3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. IV. New method for removal of 2,2,2-trichloroethyl group and 31P NMR as a new tool for analysis of deblocking of internucleotide phosphate protecting groups.

Authors:  R W Adamiak; E Biala; R Kierzek; A Kraszewski; W T Markiewicz; J Stawiński
Journal:  Nucleic Acids Res       Date:  1977-07       Impact factor: 16.971

4.  Synthesis of human insulin gene. Part I. Development of reversed-phase chromatography in the modified triester method. Its application in the rapid and efficient synthesis of eight deoxyribooligonucleotides fragments constituting human insulin A DNA.

Authors:  H M Hsiung; R Brousseau; J Michniewicz; S A Narang
Journal:  Nucleic Acids Res       Date:  1979-04       Impact factor: 16.971

5.  Protected deoxyribonucleoside-3' aryl phosphodiesters as key intermediates in polynucleotide synthesis. Construction of an icosanucleotide analogous to the sequence at the ends of Rous sarcoma virus 35S RNA.

Authors:  G R Gough; C K Singleton; H L Weith; P T Gilham
Journal:  Nucleic Acids Res       Date:  1979-04       Impact factor: 16.971

6.  New, ionic side-products in oligonucleotide synthesis: formation and reactivity of fluorescent N-/purin-6-yl/pyridinium salts.

Authors:  R W Adamiak; E Biała; B Skalski
Journal:  Nucleic Acids Res       Date:  1985-04-25       Impact factor: 16.971

7.  The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/1.

Authors:  R W Adamiak; E Biała; K Grześkowiak; R Kierzek; A Kraszewski; W T Markiewicz; J Okupniak; J Stawiński; M Wiewiórowski
Journal:  Nucleic Acids Res       Date:  1978-06       Impact factor: 16.971

8.  Further improvements on the phosphotriester synthesis of deoxyribooligonucleotides and the oligonucleotide directed site-specific mutagenesis of E. coli lipoprotein gene.

Authors:  H Hsiung; S Inouye; J West; B Sturm; M Inouye
Journal:  Nucleic Acids Res       Date:  1983-05-25       Impact factor: 16.971

9.  Hot start PCR with heat-activatable primers: a novel approach for improved PCR performance.

Authors:  Alexandre V Lebedev; Natasha Paul; Joyclyn Yee; Victor A Timoshchuk; Jonathan Shum; Kei Miyagi; Jack Kellum; Richard I Hogrefe; Gerald Zon
Journal:  Nucleic Acids Res       Date:  2008-09-16       Impact factor: 16.971

10.  Synthesis of oligodeoxynucleotides using fully protected deoxynucleoside 3'-phosphoramidite building blocks and base recognition of oligodeoxynucleotides incorporating N3-cyano-ethylthymine.

Authors:  Hirosuke Tsunoda; Tomomi Kudo; Akihiro Ohkubo; Kohji Seio; Mitsuo Sekine
Journal:  Molecules       Date:  2010-10-27       Impact factor: 4.411
  10 in total

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