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Literature DB >> 3457366

Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.

J E Marugg, E de Vroom, C E Dreef, M Tromp, G A van der Marel, J H van Boom.

Abstract

Dinucleoside methylphosphonates can easily be prepared starting from properly protected d-nucleosides and the bifunctional phosphorylating reagent methyl-O,O-bis(1-benzotriazolyl)phosphate. Separation of the diastereoisomers of 5'-DMTR-d-Ap(Me)T-3'-lev affords optically pure dinucleoside methylphosphonates which, after removal of the 3'-levulinoyl group, have been used for the synthesis of the two optically pure diastereoisomers of the hexamer d-CpGpAp(Me)TpCpG. Further, a one-pot procedure for the preparation of uridine-3',5'-cyclic methylphosphonate will be described. We also found that 3',5'-methylphosphonate linkages in RNA are not stable towards mild acid treatment.

Entities: Chemical

Mesh：

Substances：

Year: 1986 PMID： 3457366 PMCID： PMC339650 DOI： 10.1093/nar/14.5.2171

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

12 in total

1. The synthesis of oligoribonucleotides. II. Methoxymethylidene derivatives of ribonucleosides and 5'-ribonucleotides.

Authors: B E Griffin; M Jarman; C B Reese; J E Sulston
Journal: Tetrahedron Date: 1967-05 Impact factor: 2.457

2. 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

3. Polymer supported DNA synthesis using hydroxybenzotriazole activated phosphotriester intermediates.

Authors: J E Marugg; N Piel; L W McLaughlin; M Tromp; G H Veeneman; G A van der Marel; J H van Boom
Journal: Nucleic Acids Res Date: 1984-11-26 Impact factor: 16.971

4. Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.

Authors: J E Marugg; C van den Bergh; M Tromp; G A van der Marel; W J van Zoest; J H van Boom
Journal: Nucleic Acids Res Date: 1984-12-11 Impact factor: 16.971

5. 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

6. 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

7. Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNA.

Authors: A Murakami; K R Blake; P S Miller
Journal: Biochemistry Date: 1985-07-16 Impact factor: 3.162

Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.

1. The synthesis of oligoribonucleotides. II. Methoxymethylidene derivatives of ribonucleosides and 5'-ribonucleotides.

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

3. Polymer supported DNA synthesis using hydroxybenzotriazole activated phosphotriester intermediates.

4. Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.

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

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

7. Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNA.

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

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

10. Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approach.

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

2. Synthesis of nucleic acid methylphosphonothioates.

3. The application of the AMB protective group in the solid-phase synthesis of methylphosphonate DNA analogues.

4. A new approach to the synthesis of the 5'-deoxy-5'-methylphosphonate linked thymidine oligonucleotide analogues.