title: Synthesis of a glycosylated peptide thioester by the Boc strategy and its application to segment condensation.
abstract: The synthesis of a chitobiosylated peptide thioester by the t-butoxycarbonyl (Boc) strategy is demonstrated. Boc-Asn carrying benzyl-protected chitobiose was introduced during application of the Boc mode solid-phase method. HF treatment of the resulting protected peptide resin gave the desired chitobiosylated peptide thioester. This thioester was used to prepare the peptide sequence derived from extracellular matrix metalloproteinase inducers (emmprin) (34-94), (34-118) and (22-118) by the thioester segment condensation method. The conformation of these glycopeptides is characterized by circular dichroism (CD) spectral measurement.
authors.affiliation: Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Kanagawa.
authors.forename: Eiichiro
authors.initials: E
authors.lastname: Haginoya
authors.forename: Hironobu
authors.initials: H
authors.lastname: Hojo
authors.forename: Yuko
authors.initials: Y
authors.lastname: Nakahara
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nakahara
authors.forename: Kazuki
authors.initials: K
authors.lastname: Nabeshima
authors.forename: Bryan P
authors.initials: BP
authors.lastname: Toole
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Watanabe
mesh_terms: D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004952:Esters / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D008969:Molecular Sequence Data; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004952:Esters; D006020:Glycopeptides; D013438:Sulfhydryl Compounds