Gem difluorinated c-glycopeptides, their preparation and their use for the preservation of biological materials and/or in cryosurgery

Abstract

The invention concerns a gem-difluorinated C-glycopeptide compound of formula (I) in which N is an integer between 1 and 5, R<4>= H, AA1, AA1-AA2 and R<5>= OH, AA1, AA1.AA2, with AA1, and AA2 are independents and representing amino acids with a non-functionalised side chain and R<1>, R<2>, R<3> are independent groups and one of them is egal to formula (II), in which n is an integer between 3 and 4, Y, Y' are independent groups in which Y, Y'= H, OR, N3, NR'R'', SR''', where R = H, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, acetate group, R', R'' = H, alkyl, allyl, benzyl, tosylate group, C(=0)-alkyl, C(=O)-Bn, R''' = H, alkyl, acetate group, R<6> is notably a group H, CH3, CH2OH, CH2-Glycoside group, CH2-OGP in which GP is a protector group such as an alkyl, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tertbutyldiphenylsilyl, acetate group, and R<7> = OH, OGP', NH2, N3, NHGP', NGP'GP'' in which GP' and GP'' is or not a protector group such as an alkyl, benzyl, trimethylsilyl, tertbutyldimethylsilyl, tert-butyldiphenylsilyl, acetate group, and R is a hydrogen atom H or a free or protected alcohol function. It applies notably to preservation of biological materials and to cryosurgery.

Description

technical field [0001] The present invention relates to a method for the synthesis of gem-difluorinated C-glycopeptide compounds. It is particularly, but not exclusively, useful for the preparation of compounds or compositions which are especially useful for preserving biological materials and for use in cryosurgery. Background technique [0002] Antifreeze biological compounds are present in the natural environment, especially glycoproteins. For example, in some fish there are compounds that allow these fish to survive in cryogenic environments, ie, at temperatures near or below zero. [0003] Furthermore, it is known that when water freezes, this phenomenon is accompanied by an increase in volume due to the three-dimensional growth of ice. [0004] This increase in volume, and the resulting infiltration, causes severe damage in living tissue: cell membranes are ruptured, blood flow stops and the cellular microstructure is disturbed. [0005] For many years, scientists h...

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Problems solved by technology

[0023] In addition, several studies have reported that certain concentrations (5-10 mg / ml) of antifreeze glycoproteins produce needle-shaped ice crystals, which increase the likelihood of cell rupture and death during freezing

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