The Revised Structure of the Cyclic Octapeptide Surugamide A

被引：18

作者：

Matsuda, Kenichi ^{[1
]}

Kuranaga, Takefumi ^{[1
]}

Sano, Ayae ^{[1
]}

Ninomiya, Akihiro ^{[2
]}

Takada, Kentaro ^{[2
]}

Wakimoto, Toshiyuki ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Univ Tokyo, Grad Sch Agr & Life Sci, Tokyo 1138657, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2019年 / 67卷 / 05期

关键词：

marine natural product; structural revision; non-ribosomal peptide; D-amino acid; BIOSYNTHETIC GENE-CLUSTER; AMINO-ACID-ANALYSIS; NATURAL-PRODUCTS; REAGENT;

D O I：

10.1248/cpb.c19-00002

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：476 / 480

页数：5

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