Peptide and o-glycan inhibitors of selectin mediated...

Details Peptide and o-glycan inhibitors of selectin mediated... Peptide and o-glycan inhibitors of selectin mediated...

C - Chemistry, Metallurgy

07

K

C07K 14/705 (2006.01) A61K 31/70 (2006.01) A61K 38/14 (2006.01) A61K 38/17 (2006.01) C07H 3/06 (2006.01) C07H 7/02 (2006.01) C07K 9/00 (2006.01) C12N 5/10 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2228512

Tyrosine sulfate on PSGL-1, particularly at least one of residues (46, 48) and (51), functions in conjunction with sialylated and fucosylated glycans, most preferably Thr-57, to mediate high affinity binding to P-selectin. PSGL-1 O- glycans have been determined to consist of disialylated or neutral forms of the core-2 tetrasaccharide Gal.beta.14G1cNAc.beta.16(Gal.beta.13)GalNAcOH. A minority of the O-glycans are .alpha.1,3 fucosylated that occur as two major species containing the sialyl Lewis x antigen - one species is a disialylated, monofucosylated glycan of formula (I), and the other is a monosialylated, trifucosylated glycan having a polylactosamine backbone of formula (II), wherein R = H, OH, another sugar or an aglycone such as an amino acid.

Le sulfate de tyrosine présent sur le PSGL-1 (ligand-1 de glycoprotéine de P-sélectine), en particulier au moins l'un des résidus (46, 48) ou (51), opère en conjonction avec les glycanes sialylés et fucosylés, de préférence le Thr-57, pour induire une liaison de forte affinité à la sélectine P. On a pu établir que les O-glycanes présents sur le PSGL-1 consistent en des formes neutres ou disialylées du noyau 2 tétrasaccharide Gal.beta.1?4G1cNAc.beta.1?6(Gal.beta.1?3)GalNAcOH. Les O-glycanes sont en minorité des .alpha.1,3 fucosylées qui apparaissent sous la forme de deux espèces principales refermant l'antigène x de Lewis sialyle - dont l'une est un glycane disialylé monofucosylé de la formule (I), et l'autre est un glycane monosialylé trifucosylé présentant un squelette polylactosamine de la formule (II), considérant que R = H, OH, un autre sucre ou un aglycone tel qu'un acide aminé.

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