3'-(4'-) nonradioactively tagged nucleosides and nucleotides...

C - Chemistry – Metallurgy – 07 – H

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C07H 19/06 (2006.01) A61K 31/70 (2006.01) C07H 21/00 (2006.01) C07J 51/00 (2006.01) C07K 5/00 (2006.01) C07K 5/06 (2006.01) C07K 5/103 (2006.01) C07K 7/02 (2006.01) C07K 9/00 (2006.01) C12Q 1/68 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2190982

Nucleosides or nucleotides of the general formula (1) modified at the 3'(2') position Image (1) in which R': represents hydrogen, mono-, di- or triphosphate, alkylphosphonate, dialkylphosphinate or phosphoramidite X: represents oxygen, nitrogen, carbon or sulphur Y: represents oxygen, nitrogen or sulphur Z: represents a hydrogen, hydroxyl, amino or thiol group R: denotes a spacer group to which a non- radioactive, detectable group or an effector molecule is bound base: represents a purine or pyrimidine base or a deazapurine or derivatives thereof n: is 0 or 1, a process for the production of the compounds and their use in the analysis of nucleic acids and for the production of pharmaceutical agents. 3'-Amino-3'- deoxynucleotide fluoresceins in which the fluorescein group is bound to the sugar via mono-, di- and tetra- glycine units have proven to be particularly advantageous for sequencing.

L'invention concerne des nucléosides ou des nucléotides modifiés en position 3'-(4') de la formule générale (1) dans laquelle R' désigne hydrogène, mono-, di- ou triphosphate, alkylphosphonate, dialkylphosphinate ou phosphoramidite, X désigne oxygène, azote, carbone ou soufre, Y désigne oxygène, azote ou soufre, Z désigne hydrogène, un groupe hydroxyle, amino ou thiol, R désigne un groupement espaceur auquel est lié un groupe détectable non radioactif ou une molécule effectrice, base désigne purine, base de pyrimidine ou désazapurines ou leurs dérivés, n vaut 0 ou 1. L'invention concerne également un procédé qui permet de préparer ces composés, ainsi que leur utilisation dans l'analyse d'acide nucléique et dans la préparation de médicaments. Les 3'-amino-3'-fluorescéines de desoxynucléotide dans lesquelles le groupe fluorescéine est lié à la saccharose par l'intermédiaire d'unités mono-, di- et tétraglycine, se sont avérées particulièrement avantageuses lors du séquençage.

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