Literature DB >> 450712

Fluoride ion catalyzed alkylation of purines, pyrimidines, nucleosides and nucleotides using alky halides.

K K Ogilvie, S L Beaucage, M F Gillen, D Entwistle, M Quilliam.   

Abstract

Alkyl halides react rapidly with purines and pyrimidines in the presence of fluoride ion. Alkylation of thymidine leads to novel dimeric nucleoside derivatives bridged through N3. Alkylation of thymidine mono and dinucleotides leads to alkylation at the base (N3) as well as diester and triester formation at the phosphate.

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Year:  1979        PMID： 450712      PMCID： PMC327801          DOI： 10.1093/nar/6.4.1695

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


  11 in total

1.  Reactions of cytidine with 7-bromomethylbenz(a)anthracene, benzyl bromide, and p-methoxybenzyl bromide. Ratio of amino to 3 substitution.

Authors:  R Shapiro; S J Shiuey
Journal:  J Org Chem       Date:  1976-04-30       Impact factor: 4.354

Review 2.  The chemical effects of nucleic acid alkylation and their relation to mutagenesis and carcinogenesis.

Authors:  B Singer
Journal:  Prog Nucleic Acid Res Mol Biol       Date:  1975

3.  N-alkylation of purines with alkyl esters of phosphorus oxy acids.

Authors:  K Yamauchi; M Hayashi; M Kinoshita
Journal:  J Org Chem       Date:  1975-02-07       Impact factor: 4.354

4.  Reaction of cytidine with ethylating agents.

Authors:  L Sun; B Singer
Journal:  Biochemistry       Date:  1974-04-23       Impact factor: 3.162

5.  Controlled interaction between nucleic acid bases. Intramolecular stacking interactions between two adenine rings.

Authors:  N J Leonard; K Ito
Journal:  J Am Chem Soc       Date:  1973-06-13       Impact factor: 15.419

6.  Reaction of guanosine with ethylating agents.

Authors:  B Singer
Journal:  Biochemistry       Date:  1972-10-10       Impact factor: 3.162

7.  Simple models of nucleic acid interactions. 1. Base--base interactions in 1,2-Di)adenosin-N6-yl)ethane and 1,4-Di(adenosin-N6-yl)butane.

Authors:  J Zemlicka; J Owens
Journal:  J Org Chem       Date:  1977-02-04       Impact factor: 4.354

8.  A general transesterification method for the synthesis of mixed trialkyl phosphates.

Authors:  K K Ogilvie; S L Beaucage; N Theriault; D W Entwistle
Journal:  J Am Chem Soc       Date:  1977-02-16       Impact factor: 15.419

9.  Aminoacyl derivatives of "bridged" nucleosides: chemical synthesis and substrate activity of 2'(3')-O-(N-acetyl)-L-leucyl-2''(3'')-O-L-phenylalanyl-(1,2-diadenosin-N6-yl)ethane, a spacer probe for ribosomal peptidyltransferase.

Authors:  C D Li; P Bhuta; J Zemlicka
Journal:  Biochemistry       Date:  1978-06-27       Impact factor: 3.162

10.  Simple models of nucleic acid interactions 2. Aminoacyl derivatives of "bridged" nucleosides: Synthesis of 2'(3')-O-L-phenylalanyl- and 2'(3')-O-L-leucyl-1,2-di(adenosin-N6-yl)ethane.

Authors:  C Li; J Zemlicka
Journal:  J Org Chem       Date:  1977-02-18       Impact factor: 4.354
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  1 in total

1.  Fluoride ion catalyzed alkylation of nucleic acid derivatives using trialkyl phosphates, dialkyl sulfates and alkyl methanesulfonates.

Authors:  K K Ogilvie; S L Beaucage; M F Gillen; D W Entwistle
Journal:  Nucleic Acids Res       Date:  1979       Impact factor: 16.971
  1 in total

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