Synthesis and characterization of nucleobase functionalized monothiophenes

Thiophenes bearing nucleobase moieties have been prepared using 2-bromo-1-thiophen-3-yl-ethanone. The synthesis of a series of nucleobase functionalized thiophene monomers has been accomplished through the reaction of 2-bromo-1-thiophen-3-yl-ethanone with the corresponding DNA base anion. The distin...

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Bibliographic Details
Published in:Tetrahedron letters 2010-10, Vol.51 (41), p.5483-5485
Main Authors: McTiernan, Christopher D., Chahma, M’hamed
Format: Article
Language:English
Subjects:
Amines
Anions
Deoxyribonucleic acid
Monomers
Nucleosides
Synthesis (chemistry)
Tetrahedrons
Thiophenes
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Summary:Thiophenes bearing nucleobase moieties have been prepared using 2-bromo-1-thiophen-3-yl-ethanone. The synthesis of a series of nucleobase functionalized thiophene monomers has been accomplished through the reaction of 2-bromo-1-thiophen-3-yl-ethanone with the corresponding DNA base anion. The distinctive p K a values for the various amine groups in the nucleobases provided a pathway for the creation of specific anions through selective deprotonation of these groups. Using the appropriate anion it is possible to create an amine linkage between the thiophene and nucleobase that is, analogous to that found between the deoxyribose sugar and nucleobase, in the biologically occurring nucleoside.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.08.034