Insulinotropic peptide synthesis using solid and solution...

Details Insulinotropic peptide synthesis using solid and solution... Insulinotropic peptide synthesis using solid and solution...

C - Chemistry, Metallurgy

07

K

C07K 14/605 (2006.01) A61K 38/22 (2006.01) A61K 38/26 (2006.01) C07K 14/575 (2006.01)

Patent

CA 2703113

The present invention relates to the preparation of insulinotropic peptides comprising at least two glutamic acid residues in direct sequence (Glu-Glu) that are synthesized using a solid and solution phase ("hybrid") approach. Generally, the approach includes synthesizing three different peptide intermediate fragments using solid phase chemistry. Solution phase chemistry is then used to add additional amino acid material to one of the fragments. The fragments are then coupled together in the solution phase. The use of a pseudoproline in one of the fragments eases solid phase synthesis of that fragment and also eases subsequent solution phase coupling of this fragment to other fragments. The present invention is very useful for forming insulinotropic peptides such as exenatide(1-39) and its counterparts.

L'invention concerne la préparation de peptides insulinotropes contenant au moins deux résidus d'acide glutamique en séquence directe (Glu-Glu) qui sont synthétisés à l'aide d'une technique hybride faisant appel à une phase solide et à une phase en solution. L'approche comprend de manière générale la synthèse de trois fragments intermédiaires différents de peptides par voie chimique en phase solide. Une méthode chimique en solution est ensuite utilisée pour ajouter de la matière aminoacide supplémentaire à l'un des fragments. Les fragments sont ensuite couplés entre eux dans la phase en solution. L'utilisation d'une pseudoproline dans l'un des fragments facilite la synthèse en phase solide dudit fragment et facilite également le couplage ultérieur, en solution, dudit fragment à d'autres fragments. La présente invention est très utile pour former des peptides insulinotropes tels que exenatide(1-39) et ses dérivés.

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