Literature DB >> 6894029

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

A K Seth, E Jay.   

Abstract

The efficiencies and problems of sulfonation of several condensing reagents for deoxyoligoribonucleotide synthesis have been studied. While 2,4,6-triisopropylbenzenesulfonyl chloride (TPSC1) gave very low yield and slow rate of coupling, the new 1:3 mixture of TPSC1 and tetrazole afforded excellent yield and extremely fast rate of reaction with the lowest rate of sulfonation. The difference and advantages of this mixture over triisopropylbenzenesulfonyl tetrazole (TPSTe) and mesitylenesulfonyl tetrazole (MSTe) are discussed. Mechanisms for the coupling reactions with these condensing reagents to account for the difference in their rates and yields of coupling are discussed.

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Year:  1980        PMID： 6894029      PMCID： PMC324313          DOI： 10.1093/nar/8.22.5445

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


  11 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.  Chemical synthesis and sequence studies of deoxyribooligonucleotides which constitute the duplex sequence of the lactose operator of Escherichia coli.

Authors:  K Itakura; N Katagiri; S A Narang; C P Bahl; K J Marians; R Wu
Journal:  J Biol Chem       Date:  1975-06-25       Impact factor: 5.157

3.  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

4.  Chemical synthesis of versatile adaptors for molecular cloning.

Authors:  C P Bahl; R Wu; R Brousseau; A K Sood; H M Hsiung; S A Narang
Journal:  Biochem Biophys Res Commun       Date:  1978-04-14       Impact factor: 3.575

5.  Total synthesis of the gene for an alanine transfer ribonucleic acid from yeast.

Authors:  K L Agarwal; H Büchi; M H Caruthers; N Gupta; H G Khorana; K Kleppe; A Kumar; E Ohtsuka; U L Rajbhandary; J H Van de Sande; V Sgaramella; H Weber; T Yamada
Journal:  Nature       Date:  1970-07-04       Impact factor: 49.962

6.  Total synthesis of the structural gene for the precursor of a tyrosine suppressor transfer RNA from Escherichia coli. 1. General introduction.

Authors:  H G Khorana; K L Agarwal; P Besmer; H Büchi; M H Caruthers; P J Cashion; M Fridkin; E Jay; K Kleppe; R Kleppe; A Kumar; P C Loewen; R C Miller; K Minamoto; A Panet; U L RajBhandary; B Ramamoorthy; T Sekiya; T Takeya; J H van de Sande
Journal:  J Biol Chem       Date:  1976-02-10       Impact factor: 5.157

7.  Synthesis of the human insulin gene. Part II. Further improvements in the modified phosphotriester method and the synthesis of seventeen deoxyribooligonucleotide fragments constituting human insulin chains B and mini-CDNA.

Authors:  W L Sung; H M Hsiung; R Brousseau; J Michniewicz; R Wu; S A Narang
Journal:  Nucleic Acids Res       Date:  1979-12-20       Impact factor: 16.971

8.  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

9.  Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides.

Authors:  J Stawinski; T Hozumi; S A Narang; C P Bahl; R Wu
Journal:  Nucleic Acids Res       Date:  1977-02       Impact factor: 16.971

10.  A synthetic tyrosine suppressor tRNA gene with an altered promoter sequence. Its cloning and relative expression in vivo.

Authors:  M J Ryan; R Belagaje; E L Brown; H J Fritz; H G Khorana
Journal:  J Biol Chem       Date:  1979-11-10       Impact factor: 5.157
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  12 in total

1.  Fluorescent labelling of tRNA and oligodeoxynucleotides using T4 RNA ligase.

Authors:  R Cosstick; L W McLaughlin; F Eckstein
Journal:  Nucleic Acids Res       Date:  1984-02-24       Impact factor: 16.971

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

Review 3.  Recent developments in the chemical synthesis of polynucleotides.

Authors:  E Ohtsuka; M Ikehara; D Söll
Journal:  Nucleic Acids Res       Date:  1982-11-11       Impact factor: 16.971

4.  Improved rapid phosphotriester synthesis of oligodeoxyribonucleotides using oxygen-nucleophilic catalysts.

Authors:  V A Efimov; O G Chakhmakhcheva
Journal:  Nucleic Acids Res       Date:  1985-05-24       Impact factor: 16.971

5.  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

6.  General scheme of the phosphotriester condensation in the oligodeoxyribonucleotide synthesis with arylsulfonyl chlorides and arylsulfonyl azolides.

Authors:  V F Zarytova; D G Knorre
Journal:  Nucleic Acids Res       Date:  1984-02-24       Impact factor: 16.971

7.  Gene expression: chemical synthesis of E. coli ribosome binding sites and their use in directing the expression of mammalian proteins in bacteria.

Authors:  E Jay; A K Seth; J Rommens; A Sood; G Jay
Journal:  Nucleic Acids Res       Date:  1982-10-25       Impact factor: 16.971

8.  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

9.  Pre-activation strategy for oligodeoxyribonucleotide synthesis using triaryloxydichlorophosphoranes in the phosphotriester method.

Authors:  H Hotoda; T Wada; M Sekine; T Hata
Journal:  Nucleic Acids Res       Date:  1989-07-11       Impact factor: 16.971

10.  Construction of a general vector for efficient expression of mammalian proteins in bacteria: use of a synthetic ribosome binding site.

Authors:  G Jay; G Khoury; A K Seth; E Jay
Journal:  Proc Natl Acad Sci U S A       Date:  1981-09       Impact factor: 11.205
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