Linker-Free Fluorophore-Labeled Oligonucleotides: Synthesis of 3′-Fluoresceinylthymidine Building Blocks and their Coupling Reactions

Autor:	Clemens Richert, Eric Kervio, Niels Griesang
Rok vydání:	2005
Předmět:	Phosphoramidite Fluorophore Oligonucleotide Stereochemistry Organic Chemistry Catalysis Coupling reaction Residue (chemistry) chemistry.chemical_compound Solid-phase synthesis chemistry Nucleic acid heterocyclic compounds Linker
Zdroj:	Synthesis. :2327-2334
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2005-870024
Popis:	Reported here are the syntheses of two thymidine derivatives with an amide-linked 6-carboxyfluorescein residue at their 3'-position that are suitable for the synthesis of fluorophore-labeled oligonucleotides. The first isa 5'-phosphoramidite with a pivaloyl-protected carboxyfluorescein residue in the lactone form. It was prepared from 3'-azido-3'-deoxythymidine (AZT) in three steps and 73% overall yield and coupled on solid support. The second is an imidazolide of thymidine 5'-monophosphate that was obtained from AZT in five steps and 48% overall yield. The imidazolide can be coupled to amino-terminated nucleic acids in aqueous solution.
Databáze:	OpenAIRE
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