Synthesis of a glycosylated peptide thioester by the Boc strategy and its application to segment condensation.
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.
Haginoya
Eiichiro
E
Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Kanagawa.
Hojo
Hironobu
H
Nakahara
Yuko
Y
Nakahara
Yoshiaki
Y
Nabeshima
Kazuki
K
Toole
Bryan P
BP
Watanabe
Yasushi
Y
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*
D004952:Esters; D006020:Glycopeptides; D013438:Sulfhydryl Compounds