Branched building units for synthesizing cyclic peptides

C - Chemistry – Metallurgy – 07 – K

Patent

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C07K 5/02 (2006.01) C07C 229/36 (2006.01) C07C 237/10 (2006.01) C07C 271/20 (2006.01) C07C 271/22 (2006.01) C07K 5/06 (2006.01) C07K 5/065 (2006.01)

Patent

CA 2315222

The present invention relates to building units suitable for the synthesis of backbone cyclized peptides. The building units of this invention have structures of the formula (I): X-AAm-U-AAp-Y wherein AAm and AAp are residues of natural or synthetic amino acids and U is C.alpha.ON[(CH2)n+1W] or (C.alpha.H2N)[CO(CH2)qW], in which C.alpha. is a carbon atom and is the .alpha. carbon of AAm if m > 0. W is NH-X or COY, and X is H, Boc, Z, Fmoc, or Alloc while Y is the hydroxyl group of a carboxylic acid moiety or a carboxylic acid protecting group. The letter m refers to an integer from 0 to 10; n is a number from 0 to 6; p is a number from 1 to 10; and q is a number from 1 to 6. The present invention is also directed to methods of synthesizing building units of formula (I) via different routes.

La présente invention concerne des unités structurales pouvant être utilisées pour synthétiser des peptides à squelette cyclisé. Les unités structurales de cette invention présentent des structures de formule (I): X-AA¿m?-U-AA¿p?-Y, dans laquelle AA¿m? et AA¿p? représentent des restes d'acides aminés naturels ou synthétiques, et U représente C?.alpha.¿ON[(CH¿2?)¿n+1?W] ou ?( C?.alpha.¿H¿2?N)[CO(CH¿2?)¿q?W], C?.alpha.¿ représentant un atome de carbone et l'atome .alpha. de AA¿m? si m est supérieur à 0. W représente NH-X ou COY, et X représente H, Boc, Z, Fmoc, ou Alloc, alors que Y représente le groupe hydroxyle d'un fragment d'acide carboxylique ou un groupe protecteur d'acide carboxylique. La lettre m désigne un nombre entier variant entre 0 et 10; n représente un chiffre situé entre 0 et 6; p représente un chiffre entre 1 et 10; et q désigne un chiffre allant de 1 à 6. La présente invention concerne également des méthodes permettant de synthétiser des unités structurales de formule (I), selon différents processus.

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