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Literature DB >> 226943

Synthesis and enzymatic properties of deoxyribooligonucleotides containing methyl and phenylphosphonate linkages.

Abstract

Chemical methods for the synthesis of short deoxyribooligonucleotides containing methyl and phenylphosphonodiester linkages have been developed. The interaction of two such nonionic dinucleotide analogs, T(pCH3)T and T(pC6H5)T, with several enzymes has been investigated. Because of the phosphonate linkage each dinucleotide exists as a diastereomeric pair as shown by thin layer chromatography and enzymatic studies. Both isomers of each dinucleotide can be phosphorylated by T4-polynucleotide kinase in the presence of [gamma-32P]ATP. Only one of the diastereoisomers of each dinucleotide is slowly hydrolyzed by snake venom phosphodiesterase and acts as an inhibitor of the enzyme-catalyzed hydrolysis of 5'-labeled oligothymidylic acid. Both isomers of each dinucleotide analog are completely resistant to hydrolysis by spleen phosphodiesterase.

Entities: Chemical

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Year: 1979 PMID： 226943 PMCID： PMC327914 DOI： 10.1093/nar/6.9.3009

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

10 in total

1. A new method for sequencing DNA.

Authors: A M Maxam; W Gilbert
Journal: Proc Natl Acad Sci U S A Date: 1977-02 Impact factor: 11.205

2. Physical characterization and simultaneous purification of bacteriophage T4 induced polynucleotide kinase, polynucleotide ligase, and deoxyribonucleic acid polymerase.

Authors: A Panet; J H van de Sande; P C Loewen; H G Khorana; A J Raae; J R Lillehaug; K Kleppe
Journal: Biochemistry Date: 1973-12-04 Impact factor: 3.162

3. DNA sequence analysis: a general, simple and rapid method for sequencing large oligodeoxyribonucleotide fragments by mapping.

Authors: E Jay; R Bambara; R Padmanabhan; R Wu
Journal: Nucleic Acids Res Date: 1974-03 Impact factor: 16.971

4. Duplex formation of a nonionic oligo(deoxythymidylate) analogue (heptadeoxythymidylyl-(3'-5')-deoxythymidine heptaethyl ester (d-(Tp(Et))7T)) with poly(deoxyadenylate). Evaluation of the electrostatic interaction.

Authors: R C Pless; P O Ts'o
Journal: Biochemistry Date: 1977-03-22 Impact factor: 3.162

5. Chemical synthesis of a self-complementary octanucleotide, dG-G-T-T-A-A-C-C by a modified triester method.

Authors: K L Agarwal; F Riftina
Journal: Nucleic Acids Res Date: 1978-08 Impact factor: 16.971

6. 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

7. Stereochemistry of internucleotide bond formation by polynucleotide phosphorylase from Micrococcus luteus.

Authors: P M Burgers; F Eckstein
Journal: Biochemistry Date: 1979-02-06 Impact factor: 3.162

8. Nucleoside phosphonic acids. II. The synthesis of 5'-deoxythymidine 5'-phosphonic acid and its pyrophosphate derivatives.

Authors: D H Rammler; L Yengoyan; A V Paul; P C Bax
Journal: Biochemistry Date: 1967-06 Impact factor: 3.162

9. Studies on polynucleotides. CII. The use of aromatic isocyanates for selective blocking of the terminal 3'-hydroxyl group in protected deoxyribooligonucleotides.

Authors: K L Agarwal; H G Khorana
Journal: J Am Chem Soc Date: 1972-05-17 Impact factor: 15.419

10. Effects of a trinucleotide ethyl phosphotriester, Gmp(Et)Gmp(Et)U, on mammalian cells in culture.

Authors: P S Miller; L T Braiterman; P O Ts'o
Journal: Biochemistry Date: 1977-05-03 Impact factor: 3.162

10 in total

13 in total

1. Alkyl phosphotriester modified oligodeoxyribonucleotides. V. Synthesis and absolute configuration of Rp and Sp diastereomers of an ethyl phosphotriester (Et) modified EcoRI recognition sequence, d[GGAA(Et)TTCC]. A synthetic approach to regio- and stereospecific ethylation-interference studies.

Authors: K A Gallo; K L Shao; L R Phillips; J B Regan; M Koziolkiewicz; B Uznanski; W J Stec; G Zon
Journal: Nucleic Acids Res Date: 1986-09-25 Impact factor: 16.971

2. Diastereomeric dinucleoside-methylphosphonates: determination of configuration with the 2-D NMR ROESY technique.

Authors: T Löschner; J W Engels
Journal: Nucleic Acids Res Date: 1990-09-11 Impact factor: 16.971

3. Synthesis of (3'-5'),(2'-5')-linked di- and tri-adenylyl methylphosphonate analogs.

Authors: C G Wang; L X Wang; X B Yang; T Y Jiang; L H Zhang
Journal: Nucleic Acids Res Date: 1993-07-11 Impact factor: 16.971

4. Methylphosphonates as probes of protein-nucleic acid interactions.

Authors: S A Noble; E F Fisher; M H Caruthers
Journal: Nucleic Acids Res Date: 1984-04-11 Impact factor: 16.971

5. Use of methylphosphonic dichloride for the synthesis of oligonucleoside methylphosphonates.

Authors: P S Miller; C H Agris; M Blandin; A Murakami; P M Reddy; S A Spitz; P O Ts'o
Journal: Nucleic Acids Res Date: 1983-08-11 Impact factor: 16.971

6. Inhibition of acquired immunodeficiency syndrome virus by oligodeoxynucleoside methylphosphonates.

Authors: P S Sarin; S Agrawal; M P Civeira; J Goodchild; T Ikeuchi; P C Zamecnik
Journal: Proc Natl Acad Sci U S A Date: 1988-10 Impact factor: 11.205

7. Oligodeoxyribonucleoside methylphosphonates. NMR and UV spectroscopic studies of Rp-Rp and Sp-Sp methylphosphonate (Me) modified duplexes of (d[GGAATTCC])2.

Authors: M Bower; M F Summers; C Powell; K Shinozuka; J B Regan; G Zon; W D Wilson
Journal: Nucleic Acids Res Date: 1987-06-25 Impact factor: 16.971