Total Synthesis and Structural Revision of (±)-Mauritamide B.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-21 DOI:10.1021/acs.jnatprod.5c00019

Ryosuke Hirozumi, Yuta Kudo, Yuko Cho, Keiichi Konoki, Mari Yotsu-Yamashita

引用次数: 0

Abstract

Mauritamide B (1a) is a taurine-connected cyclic guanidino-bromopyrrole alkaloid originally isolated from the marine sponge Agelas linnaei. To date, the total synthesis of taurine-connected guanidino-bromopyrrole alkaloids, including this compound, has not yet been reported. Herein, a total synthesis of (±)-mauritamide B (1b) was achieved by oxidation of 2-aminoimidazole of dihydro-sventrin (10) using activated carbon and air in the presence of taurine. The synthetic precursor of 10, 4-(3-aminopropyl)-2-aminoimidazole (22), was synthesized via our original route. The NMR data of the obtained product agreed with that reported for mauritamide B (1a). However, a detailed analysis of the NMR data of synthetic (±)-mauritamide B (1b) including ¹H-¹⁵N HSQC spectrum revealed the need for a structural revision of the reported structure for mauritamide B (1b).

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

（±）-毛酰胺B的全合成及结构修正。

Mauritamide B （1a）是一种与牛磺酸相连的环胍-溴吡咯生物碱，最初是从海绵Agelas linnaei中分离出来的。迄今为止，牛磺酸连接的胍-溴吡咯生物碱的总合成，包括该化合物，尚未报道。本文在牛磺酸的存在下，利用活性炭和空气氧化二氢sventrin（10）的2-氨基咪唑，实现了（±）-mauritamide B （1b）的全合成。合成前体10,4 -（3-氨基丙基）-2-氨基咪唑（22），通过我们的原始路线合成。所得产物的核磁共振数据与莫里他胺B （1a）的报道一致。然而，对合成（±）-mauritamide B （1b）的NMR数据（包括1H-15N HSQC谱）的详细分析表明，需要对所报道的mauritamide B （1b）的结构进行结构修改。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.