期刊
CHEMICAL & PHARMACEUTICAL BULLETIN
卷 67, 期 5, 页码 476-480出版社
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c19-00002
关键词
marine natural product; structural revision; non-ribosomal peptide; D-amino acid
资金
- Takeda Science Foundation
- Asahi Glass Foundation
- SUNBOR GRANT
- NOASTEC Foundation
- Akiyama Life Science Foundation
- Japan Agency for Medical Research and Development (AMED) [18061402]
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan (JSPS KAKENHI) [JP16703511, JP18056499]
Surugamides are a group of non-ribosomal peptides isolated from marine-derived Streptomyces. Surugamide A (1) and its closely related derivatives, surugamides B-E (2-5), are D-amino acid containing cyclic octapeptides with cathepsin B inhibitory activity. The D-isoleucine (Ile), the nonproteinogenic amino acid residue embedded in 1, is less common in natural peptides because a rare C-beta-epimerization is required for its biosynthesis. Taking advantage of the synthetic route of 2 previously established by our group, we synthesized the cyclic octapeptide 1 containing D-Ile by solid phase peptide synthesis. The structure of 1 actually contains D-allo-Ile in place of D-Ile, which was corroborated by chemical syntheses and chromatographic comparisons.
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