Baumann Katharina, Kowalczyk Danuta, Gutjahr Tobias, Pieczyk Markus, Jones Claire, Wild Martin K, Vestweber Dietmar, Kunz Horst
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
Angew Chem Int Ed Engl. 2009;48(17):3174-8. doi: 10.1002/anie.200805999.
Total synthesis through block glycosylation and selective chemical O-sulfation of tyrosine residues yielded the glycopeptide recognition domain A (X=SO(3) (-)) of the P-selectin glycoprotein ligand 1, in which the terminal sialic acid of the complex hexasaccharide side chain was replaced by (S)-cyclohexyl lactic acid. In binding assays the O-sulfated structure A showed high affinity towards P-selectin, the non-sulfated towards E-selectin.
通过酪氨酸残基的块糖基化和选择性化学O-硫酸化进行的全合成产生了P-选择素糖蛋白配体1的糖肽识别结构域A(X = SO(3) (-)),其中复合六糖侧链的末端唾液酸被(S)-环己基乳酸取代。在结合试验中,O-硫酸化结构A对P-选择素显示出高亲和力,非硫酸化结构对E-选择素显示出高亲和力。