Literature DB >> 2377451

A simple method for the solid phase synthesis of oligodeoxynucleotides containing O4-alkylthymine.

Y Z Xu1, P F Swann.   

Abstract

A route to prepare the cyanoethyl-phosphoramidite monomer of O4-alkylthymine and a method for the routine solid-phase synthesis of oligodeoxynucleotides containing O4-alkylthymine are described. This method has been used to make DNA sequences up to 48 bases in length. The amino function of the adenine and guanine in the sequence were protected with the phenoxyacetyl group, and that of cytosine with the isobutyryl group. The phosphodiesters were protected with the cyanoethyl group. This allowed complete deprotection of the oligomer with alkoxide ions (methanol/1,8- diazabicyclo[5.4.0]undec-7-ene (DBU) for the oligomers containing O4-methylthymine, or ethanol/DBU for those containing O4-ethylthymine) thus avoiding the use of ammonia which is known to attack the O4-alkylthymine to form 5-methylcytosine. There was no detectable loss of the alkyl group to form thymine.

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Year:  1990        PMID： 2377451      PMCID： PMC331160          DOI： 10.1093/nar/18.14.4061

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


  8 in total

1.  Solid-phase synthesis and side reactions of oligonucleotides containing O-alkylthymine residues.

Authors:  H Borowy-Borowski; R W Chambers
Journal:  Biochemistry       Date:  1989-02-21       Impact factor: 3.162

2.  The 6-thioguanine/5-methyl-2-pyrimidinone base pair.

Authors:  H P Rappaport
Journal:  Nucleic Acids Res       Date:  1988-08-11       Impact factor: 16.971

Review 3.  O-alkyl pyrimidines in mutagenesis and carcinogenesis: occurrence and significance.

Authors:  B Singer
Journal:  Cancer Res       Date:  1986-10       Impact factor: 12.701

4.  The alkylation of 2'-deoxyguanosine and of thymidine with diazoalkanes. Some observations on o-alkylation.

Authors:  P B Farmer; A B Foster; M Jarman; M J Tisdale
Journal:  Biochem J       Date:  1973-09       Impact factor: 3.857

5.  Solid-phase synthesis of oligodeoxynucleotides containing O6-alkylguanine.

Authors:  C A Smith; Y Z Xu; P F Swann
Journal:  Carcinogenesis       Date:  1990-05       Impact factor: 4.944

6.  Synthesis and characterization of oligodeoxynucleotides containing 4-O-methylthymine.

Authors:  B F Li; C B Reese; P F Swann
Journal:  Biochemistry       Date:  1987-02-24       Impact factor: 3.162

7.  Escherichia coli polymerase I can use O2-methyldeoxythymidine or O4-methyldeoxythymidine in place of deoxythymidine in primed poly(dA-dT).poly(dA-dT) synthesis.

Authors:  B Singer; J Sági; J T Kuśmierek
Journal:  Proc Natl Acad Sci U S A       Date:  1983-08       Impact factor: 11.205

8.  Reaction products from N-methyl-N-nitrosourea and deoxyribonucleic acid containing thymidine residues. Synthesis and identification of a new methylation product, O4-methylthymidine.

Authors:  P D Lawley; D J Orr; S A Shah; P B Farmer; M Jarman
Journal:  Biochem J       Date:  1973-09       Impact factor: 3.857
  8 in total
  10 in total

1.  Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.

Authors:  Shengzhuang Tang; Jayme Cannon; Kelly Yang; Matthew F Krummel; James R Baker; Seok Ki Choi
Journal:  J Org Chem       Date:  2020-02-05       Impact factor: 4.354

2.  4-amino-1H-benzo[g]quinazoline-2-one: a fluorescent analog of cytosine to probe protonation sites in triplex forming oligonucleotides.

Authors:  F Godde; J J Toulmé; S Moreau
Journal:  Nucleic Acids Res       Date:  2000-08-01       Impact factor: 16.971

3.  Liquid Chromatography-Tandem Mass Spectrometry for the Quantification of Tobacco-Specific Nitrosamine-Induced DNA Adducts in Mammalian Cells.

Authors:  Jiapeng Leng; Yinsheng Wang
Journal:  Anal Chem       Date:  2017-08-10       Impact factor: 6.986

4.  Chemical synthesis of oligodeoxyribonucleotides containing N3- and O4-carboxymethylthymidine and their formation in DNA.

Authors:  Jianshuang Wang; Yinsheng Wang
Journal:  Nucleic Acids Res       Date:  2008-11-28       Impact factor: 16.971

5.  The synthesis of oligoribonucleotides containing N6-alkyladenosines and 2-methylthio-N6-alkyladenosines via post-synthetic modification of precursor oligomers.

Authors:  Elzbieta Kierzek; Ryszard Kierzek
Journal:  Nucleic Acids Res       Date:  2003-08-01       Impact factor: 16.971

6.  Incorporation of two modified nucleosides allows selective platination of an oligonucleotide making it suitable for duplex cross-linking.

Authors:  Berta Algueró; Enrique Pedroso; Vicente Marchán; Anna Grandas
Journal:  J Biol Inorg Chem       Date:  2007-05-30       Impact factor: 3.358

7.  Replication across regioisomeric ethylated thymidine lesions by purified DNA polymerases.

Authors:  Nisana Andersen; Pengcheng Wang; Yinsheng Wang
Journal:  Chem Res Toxicol       Date:  2013-11-01       Impact factor: 3.739

8.  Fragmentation of electrospray-produced deprotonated ions of oligodeoxyribonucleotides containing an alkylated or oxidized thymidine.

Authors:  Pengcheng Wang; Renee T Williams; Candace R Guerrero; Debin Ji; Yinsheng Wang
Journal:  J Am Soc Mass Spectrom       Date:  2014-03-25       Impact factor: 3.109

9.  Synthesis and characterization of oligodeoxyribonucleotides containing a site-specifically incorporated N6-carboxymethyl-2'-deoxyadenosine or N4-carboxymethyl-2'-deoxycytidine.

Authors:  Jianshuang Wang; Yinsheng Wang
Journal:  Nucleic Acids Res       Date:  2010-05-27       Impact factor: 16.971

10.  Cytotoxic and mutagenic properties of O4-alkylthymidine lesions in Escherichia coli cells.

Authors:  Pengcheng Wang; Nicholas J Amato; Qianqian Zhai; Yinsheng Wang
Journal:  Nucleic Acids Res       Date:  2015-09-22       Impact factor: 16.971
  10 in total

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