Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation.

ABSTRACT:

Background

Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of nucleic acids.

Results

A new approach for the preparation of labeled nucleosides via intermolecular Staudinger ligation is described. Reaction of azidonucleosides with triphenylphosphine lead to iminophosphorane intermediates, which react subsequently with derivatives of coumarin or ferrocene to form coumarin or ferrocene labeled nucleosides. Fluorescent properties of coumarin labeled nucleosides are d

SUBMITTER: Kosiova I 

PROVIDER: S-EPMC1779791 | biostudies-literature | 2006 Nov

REPOSITORIES: biostudies-literature