Method for coupling, in solution, a peptide with at least...

C - Chemistry – Metallurgy – 07 – K

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C07K 1/00 (2006.01) C07K 1/107 (2006.01) C07K 7/06 (2006.01) C07K 7/08 (2006.01) C07K 14/00 (2006.01) A61K 39/00 (2006.01)

Patent

CA 2382174

The invention concerns a method for coupling a peptide with at least a compound A, of the non-peptide type, bearing a function selected among the group consisting of carboxylic acid functions and alcohol functions. The invention is characterised in that said coupling comprises a step which consists in producing, in solution, a hydrazide bond between said peptide and said compound A. The invention also concerns modified peptides essentially formed by a peptide bound by a hydrazide bond to at least a compound A as defined above, such as a lipid, a sugar, an alcohol or a fluorescent marker, as well as the uses of said modified peptides. The invention further concerns the use of N,N'-tri(Boc)hydrazinoacetic and N,N'-di(Boc)hydrazinoacetic acids to functionalize a peptide with a .alpha.-hydrazinoacetic group.

La présente invention est relative à un procédé de couplage entre un peptide et au moins un composé A, de nature non peptidique, portant une fonction sélectionnée dans le groupe constitué par les fonctions acide carboxylique et les fonctions alcool, caractérisé en ce que ledit couplage comprend une étape de réalisation, en solution, d'un lien hydrazide entre ledit peptide et ledit composé A. La présente invention est également relative à des peptides modifiés essentiellement constitués d'un peptide lié, par un lien hydrazide, à au moins un composé A tel que défini ci-dessus, tel qu'un lipide, un sucre, un alcool ou un marqueur de fluorescence, ainsi qu'aux applications de ces peptides modifiés. La présente invention est, en outre, relative à l'utilisation des acides N,N'-tri(Boc)hydrazinoacétique et N,N'- di(Boc)hydrazinoacétique pour fonctionnaliser un peptide par un groupement .alpha.-hydrazinoacétique.

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