Literature DB >> 6878043

Use of methylphosphonic dichloride for the synthesis of oligonucleoside methylphosphonates.

P S Miller, C H Agris, M Blandin, A Murakami, P M Reddy, S A Spitz, P O Ts'o.   

Abstract

Methylphosphonic dichloride was used to prepare protected deoxyribonucleoside 3'-methylphosphonate beta-cyanoethyl esters, d-[(MeO)2Tr]NpCNEt, and protected oligonucleoside methylphosphonates in solution. Reaction of d-[(MeO)2Tr]N with methylphosphonic dichloride gives d-[(MeO)2Tr]NpCl. The phosphonylation and subsequent esterification or condensation reactions are each complete within 60 min. The products are readily purified by "flash chromatography" on silica gel columns. d-[(MeO)2Tr]NpCl, or its tetrazole derivative, d-[(MeO)2Tr]Nptet, were tested as intermediates for the synthesis of oligothymidine methylphosphonates on a silica gel polymer support. The average yield per coupling step was 76% and did not increase with addition of more d-[(MeO)2Tr]TpCl. The formation of (5'-5') linked thymidine dimers indicated that the thymidine monomers are clustered closely together on the support. When N is ibuG, the yield for the coupling step on the support is very low. This may be due to steric hindrance of the 3'-phosphonate group by the N-2 isobutryl protecting group.

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Year:  1983        PMID： 6878043      PMCID： PMC326248          DOI： 10.1093/nar/11.15.5189

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


  8 in total

1.  Computer programming for nucleic acid studies. III. Calculated ultraviolet absorption spectra of protected oligodeoxyribonucleotides.

Authors:  L Kan; R W Kettell; P S Miller
Journal:  Comput Programs Biomed       Date:  1981 Sep-Dec

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

Authors:  K L Agarwal; F Riftina
Journal:  Nucleic Acids Res       Date:  1979-07-11       Impact factor: 16.971

3.  Proton nuclear magnetic resonance studies on dideoxyribonucleoside methylphosphonates.

Authors:  L S Kan; D M Cheng; P S Miller; J Yano; P O Ts'o
Journal:  Biochemistry       Date:  1980-05-13       Impact factor: 3.162

4.  Nonionic nucleic acid analogues. Synthesis and characterization of dideoxyribonucleoside methylphosphonates.

Authors:  P S Miller; J Yano; E Yano; C Carroll; K Jayaraman; P O Ts'o
Journal:  Biochemistry       Date:  1979-11-13       Impact factor: 3.162

5.  Oligothymidylate analogues having stereoregular, alternating methylphosphonate/phosphodiester backbones. Synthesis and physical studies.

Authors:  P S Miller; N Dreon; S M Pulford; K B McParland
Journal:  J Biol Chem       Date:  1980-10-25       Impact factor: 5.157

6.  Preparation of a decadeoxyribonucleotide helix for studies by nuclear magnetic resonance.

Authors:  P S Miller; D M Cheng; N Dreon; K Jayaraman; L S Kan; E E Leutzinger; S M Pulford; P O Ts'o
Journal:  Biochemistry       Date:  1980-09-30       Impact factor: 3.162

7.  Selective inhibition of Escherichia coli protein synthesis and growth by nonionic oligonucleotides complementary to the 3' end of 16S rRNA.

Authors:  K Jayaraman; K McParland; P Miller; P O Ts'o
Journal:  Proc Natl Acad Sci U S A       Date:  1981-03       Impact factor: 11.205

8.  Biochemical and biological effects of nonionic nucleic acid methylphosphonates.

Authors:  P S Miller; K B McParland; K Jayaraman; P O Ts'o
Journal:  Biochemistry       Date:  1981-03-31       Impact factor: 3.162
  8 in total
  3 in total

1.  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

2.  Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages.

Authors:  C J Marcus-Sekura; A M Woerner; K Shinozuka; G Zon; G V Quinnan
Journal:  Nucleic Acids Res       Date:  1987-07-24       Impact factor: 16.971

3.  Octa(thymidine methanephosphonates) of partially defined stereochemistry: synthesis and effect of chirality at phosphorus on binding to pentadecadeoxyriboadenylic acid.

Authors:  Z J Lesnikowski; M Jaworska; W J Stec
Journal:  Nucleic Acids Res       Date:  1990-04-25       Impact factor: 16.971
  3 in total

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