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Structures and Biosynthetic Pathway of Pulvomycins B–D: 22-Membered Macrolides from an Estuarine <i>Streptomyces</i> sp.

Kyuho Moon, Jinsheng Cui, Eunji Kim, Evan Setiawan Riandi, So Hyun Park, Woong Sub Byun, Youngju Kal, Jun Yong Park, Sunghoon Hwang, Daniel Shin, Jeongyoon Sun, Ki‐Bong Oh, Sangwon Cha, Jongheon Shin, Sang Kook Lee, Yeo Joon Yoon, Dong‐Chan Oh

2020Organic Letters27 citationsDOI

Abstract

Pulvomycins B–D (1–3) were discovered from an estuarine Streptomyces strain along with the known pulvomycin (4). The 22-membered macrocyclic lactone structures of 1–3 were determined based on the interpretation of NMR, UV, and MS data, the modified Mosher’s method, and Kishi’s bidentate chiral solvent NMR spectroscopy. Genomic analysis of the bacterial strain revealed the biosynthetic gene cluster of pulvomycin and enabled us to propose the trans-acyltransferase polyketide biosynthetic pathway. Pulvomycin D displayed potent cytotoxic activity against various cancer cell lines.

Topics & Concepts

ChemistryStereochemistryPolyketideStreptomycesStrain (injury)Gene clusterNuclear magnetic resonance spectroscopyTwo-dimensional nuclear magnetic resonance spectroscopyBiosynthesisGeneBacteriaBiochemistryBiologyGeneticsAnatomyMicrobial Natural Products and BiosynthesisSynthesis and Biological ActivitySynthetic Organic Chemistry Methods
Structures and Biosynthetic Pathway of Pulvomycins B–D: 22-Membered Macrolides from an Estuarine <i>Streptomyces</i> sp. | Litcius