Home LiteratureArticle Details
PMID: 167350 Published · ppublish English Journal Article Research Support, U.S. Gov't, P.H.S.

Solid support synthesis of oligothymidylates using phosphorochloridates and 1-alkylimidazoles.

Nucleic acids research ·Vol. 2 ·No. 6 ·1975-06-00 ·Pages 773-86

Pless RC, Letsinger RL

Abstract

A study of the synthesis of oligothymidylates via phosphotriester intermediates on a polystyrene support is described. The sequence involves condensation of a phenyl nucleoside-3' -phosphorochloridate with the 5'-hydroxyl group of the carrier bound oligonucleotide derivative in the presence of 1-methylimidazole. Conditions for preparation of the phenyl nucleo-side phosphorochloridate as well as for the condensation on the support are discussed. d-TpTpTpT was obtained in 31% overall yield from carrier bound thymidine in one series of experiments, and d-TpTpTpTpT was obtained in 9% yield in another. The cycle for addition of one nucleotide unit can be completed in about six hours.

MeSH Terms
Chlorine Imidazoles Oligonucleotides/chemical synthesis Phosphorus Acids Polystyrenes Thymine Nucleotides/chemical synthesis
Chemicals
Imidazoles Oligonucleotides Phosphorus Acids Polystyrenes Thymine Nucleotides Chlorine
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Pless R C
Letsinger R L
References (10)
10 references, click to expand
  1. [Nucleosides and nucleotides. Solid-phase synthesis of oligonucleotides on an insoluble, macroporous carrier].
    Helv Chim Acta. 1973 Mar 14;56(2):654-70 PMID: 4753797
  2. The synthesis of oligoribonucleotides. X. Preparation of 2',3'-cyclic phosphates of ribonucleosides and diribonucleoside phosphates via phosphotriester intermediates.
    J Chem Soc Perkin 1. 1973;21:2513-7 PMID: 4797713
  3. Studies on transfer ribonucleic acids and related compounds. V. Synthesis of ribonucleotides with phosphomonoester end groups on a polymer support.
    J Am Chem Soc. 1972 May 3;94(9):3229-33 PMID: 5032499
  4. [Synthesis of oligonucleotides on polymer carriers. Synthesis of oligodeoxynucleotides containing deoxyguanylic acid].
    Dokl Akad Nauk SSSR. 1971 Aug 11;199(5):1072-4 PMID: 5126559
  5. A new polymer-support method for the synthesis of ribooligonucleotide.
    J Am Chem Soc. 1971 Jun 30;93(13):3272-6 PMID: 5559599
  6. Synthesis of deoxyguanylyldeoxyguanosine on an insoluble polymer support.
    J Org Chem. 1968 Feb;33(2):708-11 PMID: 5636613
  7. Stepwise synthesis of oligodeoxyribonucleotides on an insoluble polymer support.
    J Am Chem Soc. 1966 Nov 20;88(22):5319-24 PMID: 5979268
  8. Reactions of nucleosides on polymer supports. Synthesis of thymidylylthymidylylthymidine.
    Biochemistry. 1967 May;6(5):1379-88 PMID: 6036831
  9. Oligonucleotide syntheses utilizing beta-benzoylpropionyl, a blocking group with a trigger for selective cleavage.
    J Am Chem Soc. 1967 Dec 20;89(26):7146-7 PMID: 6064358
  10. Synthetic studies of nucleic acids on polymer supports. I. Oligodeoxyribonucleotide synthesis on an insoluble polymer support.
    J Chem Soc Perkin 1. 1967;22:2438-42 PMID: 6070201
Article Info
Journal
Nucleic acids research
Abbr.
Nucleic Acids Res
ISSN
0305-1048
DOI
10.1093/nar/2.6.773
Published
1975-06-00
Pages
773-86
Language
English
Region
England
NLM ID
0411011
PMCID
PMC343465
Subset
IM
External Links
PubMed source DOI: 10.1093/nar/2.6.773 PMC Full Text View journal details
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]

Copyright © 2026.Genelibs Jinan Honghui Biotechnology Co., Ltd. 鲁ICP备20007159号-2