Bioorg Med Chem Lett. 2010 Feb 1;20(3):841-3. Epub 2010 Jan 4.

Synthesis of fluorescent nucleoside analogs as probes for 2'-deoxyribonucleoside kinases.

Li Y, Soni PB, Liu L, Zhang X, Liotta DC, Lutz S.

Source

Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA.

Abstract

We are reporting on the synthesis of fluorescent nucleoside analogs with modified sugar moieties (e.g., sugars other than ribose and 2'-deoxyribose). Four novel derivatives of the fluorescent thymidine analog 6-methyl-3-(beta-D-2'-deoxyribofuranosyl) furano-[2,3-d]pyrimidin-2-one were synthesized via Sonogashira reaction and subsequent copper-catalyzed cycloaddition. These compounds represent promising tools for studying nucleoside metabolism inside living cells, as well as for screening directed evolution libraries of 2'-deoxyribonucleoside kinases with new and improved activity for the corresponding nucleoside analogs.

PMID:: 20060716; [PubMed - indexed for MEDLINE]
PMCID: PMC2818875

Free PMC Article

Images from this publication.See all images (4) Free text

Publication Types, MeSH Terms, Substances, Grant Support

Publication Types

MeSH Terms

Substances

Grant Support

LinkOut - more resources

Full Text Sources

Other Literature Sources

COS Scholar Universe

Supplemental Content

Related citations

Directed evolution of an orthogonal nucleoside analog kinase via fluorescence-activated cell sorting. [Nucleic Acids Res. 2009]
Directed evolution of an orthogonal nucleoside analog kinase via fluorescence-activated cell sorting.
Liu L, Li Y, Liotta D, Lutz S. Nucleic Acids Res. 2009 Jul; 37(13):4472-81. Epub 2009 May 27.
Review Structure-activity relationships for phosphorylation of nucleoside analogs to monophosphates by nucleoside kinases. [Acta Biochim Pol. 1996]
Review Structure-activity relationships for phosphorylation of nucleoside analogs to monophosphates by nucleoside kinases.
Johansson NG, Eriksson S. Acta Biochim Pol. 1996; 43(1):143-60.
Identification of residues involved in the specificity and regulation of the highly efficient multisubstrate deoxyribonucleoside kinase from Drosophila melanogaster. [J Mol Biol. 2000]
Identification of residues involved in the specificity and regulation of the highly efficient multisubstrate deoxyribonucleoside kinase from Drosophila melanogaster.
Knecht W, Munch-Petersen B, Piskur J. J Mol Biol. 2000 Aug 25; 301(4):827-37.
Enzymatic phosphorylation of unnatural nucleosides. [J Am Chem Soc. 2002]
Enzymatic phosphorylation of unnatural nucleosides.
Wu Y, Fa M, Tae EL, Schultz PG, Romesberg FE. J Am Chem Soc. 2002 Dec 11; 124(49):14626-30.
Review Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases. [Pharmacol Ther. 2000]
Review Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases.
Van Rompay AR, Johansson M, Karlsson A. Pharmacol Ther. 2000 Aug-Sep; 87(2-3):189-98.

See reviews... See all...

Cited by 1 PubMed Central article

Fluorescent xDNA nucleotides as efficient substrates for a template-independent polymerase. [Nucleic Acids Res. 2011]
Fluorescent xDNA nucleotides as efficient substrates for a template-independent polymerase.
Jarchow-Choy SK, Krueger AT, Liu H, Gao J, Kool ET. Nucleic Acids Res. 2011 Mar; 39(4):1586-94. Epub 2010 Oct 14.

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
BioAssay
PubChem BioAssay experiments on the biological activities of small molecules that cite the current articles. The depositors of BioAssay data provide these references.
References for this PMC Article
Citation referenced in PubMed article. Only valid for PubMed citations that are also in PMC.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Free in PMC
Free full text articles in PMC
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Synthesis of fluorescent nucleoside analogs as probes for 2'-deoxyribonucleoside...
Synthesis of fluorescent nucleoside analogs as probes for 2'-deoxyribonucleoside kinases.
Bioorg Med Chem Lett. 2010 Feb 1 ;20(3):841-3. Epub 2010 Jan 4 .

PubMed
[Public financing of pharmaceuticals to quit smoking: utilisation and cost in Na...
[Public financing of pharmaceuticals to quit smoking: utilisation and cost in Navarra, Spain (1995-2007)].
Gac Sanit. 2010 Sep-Oct ;24(5):428-30. Epub 2010 Jul 8 .

PubMed
Human herpesvirus 6B, complete genome
Human herpesvirus 6B, complete genome
gi|9633069|ref|NC_000898.1||gnl|NCB OMES|15112

Nucleotide
Prevalence of autoantibody-negative diabetes is not rare at all ages and increas...
Prevalence of autoantibody-negative diabetes is not rare at all ages and increases with older age and obesity.
J Clin Endocrinol Metab. 2007 Jan ;92(1):88-92. Epub 2006 Oct 24 .

PubMed
Symptoms and findings predictive for the development of new retinal breaks.
Symptoms and findings predictive for the development of new retinal breaks.
Arch Ophthalmol. 2005 Apr ;123(4):479-84.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Display Settings:

Send to: