Literature DB >> 4000969

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

R W Adamiak, E Biała, B Skalski.   

Abstract

Fluorescent N-/purin-6-yl/pyridinium salts are formed in pyridine assisted phosphorylations and arenesulphonations of the hypoxanthine lactam system under various conditions including those used in oligonucleotide synthesis. The N1-methyl-N3-/purin-6-yl/imidazolium salt is generated in phosphorylation with TPSCl/1-methylimidazole as a coupling system. Both salts are representatives of a new family of ionic side-products in oligonucleotide synthesis involving hypoxanthine residues. Their isolation procedure has been developed. High reactivity of N-/purin-6-yl/pyridinium salts towards some reagents used in oligonucleotide chemistry, e.g. pyridinium mediated conversion of hypoxanthine into 6-aminopurine, can result in point mutations in synthesized oligomer.

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Year:  1985        PMID： 4000969      PMCID： PMC341209          DOI： 10.1093/nar/13.8.2989

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


  15 in total

1.  The use of arylsulfonyltriazoles for the synthesis of oligonucleotides by the triester approach.

Authors:  N Katagiri; K Itakura; S A Narang
Journal:  J Am Chem Soc       Date:  1975-12-10       Impact factor: 15.419

2.  Synthesis and reactions of a nucleoside derivative of phosphoric sulfonic anhydride. Studies related to the mechanisms of coupling reactions in the chemical synthesis of oligodeoxyribonucleotides by phosphotriester procedures.

Authors:  W Dabkowski; Z Skrzypczynski; J Michalski; N Piel; L W McLaughlin; F Cramer
Journal:  Nucleic Acids Res       Date:  1984-12-11       Impact factor: 16.971

3.  New effective method for the synthesis of oligonucleotides via phosphotriester intermediates.

Authors:  V A Efimov; S V Reverdatto; O G Chakhmakhcheva
Journal:  Nucleic Acids Res       Date:  1982-11-11       Impact factor: 16.971

4.  Chemical synthesis of genes for human insulin.

Authors:  R Crea; A Kraszewski; T Hirose; K Itakura
Journal:  Proc Natl Acad Sci U S A       Date:  1978-12       Impact factor: 11.205

5.  Nature of side-reactions in oligonucleotide synthesis involving arenesulphonyl derivatives of 3-nitro-1,2,4-triazole and related condensing agents.

Authors:  C B Reese; A Ubasawa
Journal:  Nucleic Acids Symp Ser       Date:  1980

6.  Synthesis and physical characterization of the self-complementary, alternating pyrimidine/purine hexanucleotide d[CGTACG].

Authors:  S Kuzmich; L A Marky; R A Jones
Journal:  Nucleic Acids Res       Date:  1982-10-25       Impact factor: 16.971

7.  Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides.

Authors:  W L Sung
Journal:  Nucleic Acids Res       Date:  1981-11-25       Impact factor: 16.971

8.  Some observations relating to the oximate ion promoted unblocking of oligonucleotide aryl esters.

Authors:  C B Reese; L Zard
Journal:  Nucleic Acids Res       Date:  1981-09-25       Impact factor: 16.971

9.  Rapid synthesis of oligodeoxyribonucleotides VI. Efficient, mechanised synthesis of heptadecadeoxyribonucleotides by an improved solid phase phosphotriester route.

Authors:  M L Duckworth; M J Gait; P Goelet; G F Hong; M Singh; R C Titmas
Journal:  Nucleic Acids Res       Date:  1981-04-10       Impact factor: 16.971

10.  A study of the efficiency and the problem of sulfonation of several condensing reagents and their mechanisms for the chemical synthesis of deoxyoligoribonucleotides.

Authors:  A K Seth; E Jay
Journal:  Nucleic Acids Res       Date:  1980-11-25       Impact factor: 16.971
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  5 in total

1.  Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers via intermediate O6-(benzotriazol-1-yl) derivatives.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2012-06

2.  Incorporation of reporter molecule-labeled nucleotides by DNA polymerases. I. Chemical synthesis of various reporter group-labeled 2'-deoxyribonucleoside-5'-triphosphates.

Authors:  Gerald Giller; Taurai Tasara; Bernhard Angerer; Klaus Mühlegger; Mario Amacker; Holger Winter
Journal:  Nucleic Acids Res       Date:  2003-05-15       Impact factor: 16.971

3.  Fluorescent nucleoside derivatives: Luminescence study of 4-dimethylaminopyridinium chloride derived from guanosine.

Authors:  G Wenska; B Skalski; S Paszyc; S Wnuk; R W Adamiak
Journal:  J Fluoresc       Date:  1994-12       Impact factor: 2.217

4.  Inosine.adenine base pairs in a B-DNA duplex.

Authors:  P W Corfield; W N Hunter; T Brown; P Robinson; O Kennard
Journal:  Nucleic Acids Res       Date:  1987-10-12       Impact factor: 16.971

5.  Guanine modification during chemical DNA synthesis.

Authors:  J S Eadie; D S Davidson
Journal:  Nucleic Acids Res       Date:  1987-10-26       Impact factor: 16.971
  5 in total

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