A Natural Protecting Group Strategy to Carry an Amino Acid Starter Unit in the Biosynthesis of Macrolactam Polyketide Antibiotics

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Oct 21

PMID 22010945

Citations 18

Authors

Yuji Shinohara

Fumitaka Kudo

Tadashi Eguchi

Affiliations

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Abstract

Macrolactam antibiotics are an important class of macrocyclic polyketides that contain a unique nitrogen-containing starter unit. In the present study, a set of starter biosynthetic enzymes in the macrolactam antibiotic vicenistatin was characterized. We found that the protection-deprotection strategy of the aminoacyl-ACP intermediate was critical in this system. On the basis of bioinformatics, the described pathway is also proposed as a common method for carrying amino acids in the biosynthesis of other macrolactam antibiotics.

Citing Articles

Biosynthesis of macrolactam antibiotics with β-amino acid polyketide starter units.

Kudo F J Antibiot (Tokyo). 2024; 77(8):486-498.

PMID: 38816450 PMC: 11284099. DOI: 10.1038/s41429-024-00742-2.

Semi-synthesis and structure-activity relationship study yield antibacterial vicenistatin derivatives with low cytotoxicity.

Li J, Yang Z, Shi C, Wu X, Zhou L, Liang Y J Antibiot (Tokyo). 2024; 77(4):221-227.

PMID: 38228780 DOI: 10.1038/s41429-023-00701-3.

Genome mining for macrolactam-encoding gene clusters allowed for the network-guided isolation of β-amino acid-containing cyclic derivatives and heterologous production of ciromicin A.

Seibel E, Um S, Dayras M, Bodawatta K, de Kruijff M, Jonsson K Commun Chem. 2023; 6(1):257.

PMID: 37985888 PMC: 10662134. DOI: 10.1038/s42004-023-01034-w.

Oxalactam A, a Novel Macrolactam with Potent Anti- Activity from the Endophytic Fungus .

Zhang R, Ma Y, Xu M, Wei X, Yang C, Zeng F Molecules. 2022; 27(24).

PMID: 36557941 PMC: 9788486. DOI: 10.3390/molecules27248811.

Total Biosynthesis of the Tubulin-Binding Alkaloid Colchicine.

Nett R, Sattely E J Am Chem Soc. 2021; 143(46):19454-19465.

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