title: Oligo(tyrosine sulfate)s as heparin pentasaccharide mimic: evaluation by surface noncovalent affinity mass spectrometry.
abstract: Since the discovery of anti-HIV activity in oligo(tyrosine sulfate)s in our laboratory, we have been interested in their potential as heparin pentasaccharide mimics. In this study, we investigated their interactions with synthetic heparin-binding peptides, derived from human antithrombin III (hAT III) and heparin-interacting protein (HIP), using surface noncovalent affinity mass spectrometry. We compared binding affinities to those heparin-binding peptides between oligo(tyrosine sulfate)s and several known sulfated compounds and found that oligo(tyrosine sulfate)s bind to hAT III (123-139) more strongly than a heparin-derived hexasaccharide dp6. Moreover, we found longer oligo(tyrosine sulfate) has higher binding affinity to hAT III (123-139).
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
authors.forename: Miyuki
authors.initials: M
authors.lastname: Yamaguchi
authors.forename: Tsukasa
authors.initials: T
authors.lastname: Ohmori
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Sakata
authors.forename: Masaaki
authors.initials: M
authors.lastname: Ueki
mesh_terms: D000990:Antithrombin III / Q000737:chemistry / Q000378:metabolism; D001779:Blood Coagulation Factors / Q000737:chemistry / Q000378:metabolism; D006497:Heparan Sulfate; D006801:Humans; D013058:Mass Spectrometry / Q000379:methods*; D018716:Molecular Mimicry; D009841:Oligonucleotides / Q000737:chemistry / Q000494:pharmacology; D011485:Protein Binding; D016601:RNA-Binding Proteins; D012269:Ribosomal Proteins; D013329:Structure-Activity Relationship; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000990:Antithrombin III; D001779:Blood Coagulation Factors; D006497:Heparan Sulfate; D009841:Oligonucleotides; D016601:RNA-Binding Proteins; D012269:Ribosomal Proteins; D014443:Tyrosine; C104946:RPL29 protein, human; C005662:tyrosine O-sulfate