Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-30 DOI:10.1021/acs.jnatprod.4c00972

Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino

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Abstract

Chemical investigation of the cyanobacterium Microcystis aeruginosa NIES-4285 led to the isolation of six new natural products, microginins 705 (1), 719 (2), 733A (3), 733B (4), and 733C (5), and anabaenopeptin 885 (7), and three known compounds, anabaenopeptins 871 (6), B (8), and F (9). Planar structures and absolute configurations for 1-7 were determined by 2D NMR, HRMS, and Marfey's analyses. Microginin 733C (5), and anabaenopeptins 871 (6) and 885 (7) contained a unique residue of 2-amino-5-(4-hydroxyphenyl)pentanoic acid (Ahppa): doubly homologated tyrosine (di-hTyr). The biosynthetic origin of this nonproteinogenic amino acid di-hTyr was investigated, and it was found that MaHphABCDE are involved in the production of di-hTyr. In addition, biochemical characterization of aminotransferase MaHphE showed that it is a promiscuous enzyme. This result expanded the biocatalytic toolbox for amino acid homologation.

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来自铜绿微囊藻 NIES-4285 蓝藻的双同源含酪氨酸肽及其生物合成。

通过对铜绿微囊藻 NIES-4285 进行化学研究，分离出了六种新的天然产物：微精素 705 (1)、719 (2)、733A (3)、733B (4) 和 733C (5)，以及anabaenopeptin 885 (7)，以及三种已知化合物：anabaenopeptins 871 (6)、B (8) 和 F (9)。通过二维 NMR、HRMS 和 Marfey 分析确定了 1-7 的平面结构和绝对构型。小精氨酸 733C (5)以及安纳本肽 871 (6) 和 885 (7) 含有一个独特的 2-氨基-5-（4-羟基苯基）戊酸（Ahppa）残基：双同源酪氨酸（di-hTyr）。研究人员对这种非蛋白源氨基酸 di-hTyr 的生物合成来源进行了调查，发现 MaHphABCDE 参与了 di-hTyr 的生成。此外，对转氨酶 MaHphE 的生化鉴定表明，它是一种杂合酶。这一结果扩大了氨基酸同源的生物催化工具箱。

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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.