Synthesis of a Glycosylated Peptide Thioester by the Boc Strategy and Its Application to Segment Condensation

Eiichiro HAGINOYA; Hironobu HOJO; Yuko NAKAHARA; Yoshiaki NAKAHARA; Kazuki NABESHIMA; Bryan P. TOOLE; Yasushi WATANABE

doi:10.1271/bbb.50621

Organic Chemistry Regular Paper

Synthesis of a Glycosylated Peptide Thioester by the Boc Strategy and Its Application to Segment Condensation

Eiichiro HAGINOYA, Hironobu HOJO, Yuko NAKAHARA, Yoshiaki NAKAHARA, Kazuki NABESHIMA, Bryan P. TOOLE, Yasushi WATANABE

著者情報

キーワード: glycosylated peptide thioester, solid-phase synthesis, segment condensation

ジャーナルフリー

2006 年 70 巻 6 号 p. 1338-1349

DOI https://doi.org/10.1271/bbb.50621

詳細

抄録

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.

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