5-Heteroaryl-2'-deoxyuridine Analogs. Synthesis and Incorporation into High-Affinity Oligonucleotides

A series of C-5 heteroaryl-2'-deoxyuridines were synthesized from 5-iodo-2'-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substitut...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 116; no. 13; pp. 5540 - 5544
Main Authors Gutierrez, Arnold J, Terhorst, Terry J, Matteucci, Mark D, Froehler, Brian C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.06.1994
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ACID RELATED-COMPOUNDS
AMPLIFICATION
INHIBITION
AMPLIFIERS
REAGENTS
NUCLEOSIDES
C-5
IMIDAZOLES
CAVITY SHAPED MOLECULES
DERIVATIVES
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Summary:A series of C-5 heteroaryl-2'-deoxyuridines were synthesized from 5-iodo-2'-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substituted 2'-deoxyuridine analogs gave enhanced thermal stability to complementary RNA relative to thymidine. Thermal denaturation studies showed that oligodeoxynucleotides (ODNs) containing 5-(thiazol-2-yl)-2'-deoxyuridine exhibit the highest thermal denaturation (Tm) and therefore may increase the potency of these ODNs to inhibit gene expression in a sequence specific manner.
Bibliography:ark:/67375/TPS-DWCMKCT7-0
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ObjectType-Article-2
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja00092a003