Discovery and Biosynthesis of Ureidopeptide Natural Products Macrocyclized via Indole N-acylation in Marine Microbulbifer spp. Bacteria

被引：9

作者：

Zhong, Weimao ^{[1
]}

Deutsch, Jessica M. ^{[1
]}

Yi, Dongqi ^{[1
]}

Abrahamse, Nadine H. ^{[1
]}

Mohanty, Ipsita ^{[1
,4
]}

Moore, Samuel G. ^{[1
]}

McShan, Andrew C. ^{[1
]}

Garg, Neha ^{[1
,2
]}

Agarwal, Vinayak ^{[1
,3
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biochem, 901 Atlantic Dr, Atlanta, GA 30332 USA

[2] Georgia Inst Technol, Ctr Microbial Dynam & Infect, 311 Ferst Dr, Atlanta, GA 30332 USA

[3] Georgia Inst Technol, Sch Biol Sci, 950 Atlantic Dr, Atlanta, GA 30332 USA

[4] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, 9500 Gilman Dr, La Jolla, CA 92037 USA

来源：

CHEMBIOCHEM | 2023年 / 24卷 / 12期

基金：

美国国家科学基金会;

关键词：

biosynthesis; microbulbifer; natural products; NRPS; ureido peptide; GENE CLUSTERS; PEPTIDES; SPONGE; ANABAENOPEPTIN; IDENTIFICATION; REVEALS;

D O I：

10.1002/cbic.202300190

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Commensal bacteria associated with marine invertebrates are underappreciated sources of chemically novel natural products. Using mass spectrometry, we had previously detected the presence of peptidic natural products in obligate marine bacteria of the genus Microbulbifer cultured from marine sponges. In this report, the isolation and structural characterization of a panel of ureidohexapeptide natural products, termed the bulbiferamides, from Microbulbifer strains is reported wherein the tryptophan side chain indole participates in a macrocyclizing peptide bond formation. Genome sequencing identifies biosynthetic gene clusters encoding production of the bulbiferamides and implicates the involvement of a thioesterase in the indolic macrocycle formation. The structural diversity and widespread presence of bulbiferamides in commensal microbiomes of marine invertebrates point toward a possible ecological role for these natural products.

引用

页数：7