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PMID: 226943 Published · ppublish English Journal Article Research Support, U.S. Gov't, P.H.S.

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

Nucleic acids research ·Vol. 6 ·No. 9 ·1979-07-11 ·Pages 3009-24

Agarwal KL, Riftina F

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.

MeSH Terms

Esters Kinetics Methods Methylation Oligodeoxyribonucleotides/chemical synthesis Oligonucleotides/chemical synthesis Organophosphonates Phosphoric Diester Hydrolases/metabolism Structure-Activity Relationship

Chemicals

Esters Oligodeoxyribonucleotides Oligonucleotides Organophosphonates Phosphoric Diester Hydrolases

Authors & Affiliations

2 authors, click to expand affiliations / ORCID

Agarwal K L

Riftina F

References (10)

10 references, click to expand

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Article Info

Journal

Nucleic acids research

Abbr.

Nucleic Acids Res

ISSN

0305-1048

DOI

10.1093/nar/6.9.3009

Published

1979-07-11

Pages

3009-24

Language

English

Region

England

NLM ID

0411011

PMCID

PMC327914

Subset

External Links

PubMed source DOI: 10.1093/nar/6.9.3009 PMC Full Text View journal details

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

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