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

被引：0

作者：

Phan, Chin-Soon ^{[1
]}

Ling, Zhengyi ^{[2
]}

Mehjabin, Jakia Jerin ^{[1
]}

Matsuda, Kenichi ^{[3
]}

Prakoso, Nurcahyo Iman ^{[2
,4
]}

Umezawa, Taiki ^{[1
,2
]}

Wakimoto, Toshiyuki ^{[3
]}

Okino, Tatsufumi ^{[1
,2
]}

机构：

[1] Hokkaido Univ, Fac Environm Earth Sci, Kita Ku, Sapporo 0600810, Japan

[2] Hokkaido Univ, Grad Sch Environm Sci, Kita Ku, Sapporo 0600810, Japan

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

[4] Univ Islam Indonesia, Chem Dept, Sleman 55584, Yogyakarta, Indonesia

来源：

JOURNAL OF NATURAL PRODUCTS | 2024年 / 87卷 / 11期

基金：

日本学术振兴会;

关键词：

CYCLIC-PEPTIDES; ANABAENOPEPTINS; INHIBITORS; ORIGIN; ACIDS;

D O I：

10.1021/acs.jnatprod.4c00972

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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.

引用

页码：2629 / 2639

页数：11

共 29 条

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