Biosynthesis of streptolidine involved two unexpected intermediates produced by a dihydroxylase and a cyclase through unusual mechanisms

CY Chang, SY Lyu, YC Liu, NS Hsu, CC Wu… - Angewandte …, 2014 - Wiley Online Library
Abstract Streptothricin‐F (STT‐F), one of the early‐discovered antibiotics, consists of three
components, a β‐lysine homopolymer, an aminosugar d‐gulosamine, and an unusual …

tRNA-dependent aminoacylation of an amino sugar intermediate in the biosynthesis of a streptothricin-related antibiotic

C Maruyama, H Niikura, M Izumikawa… - Applied and …, 2016 - Am Soc Microbiol
The antibiotic streptothricin (ST) possesses an amino sugar bound to an l-β-lysine (β-Lys)
residue via a peptide bond. The peptide bond formation has been shown to be catalyzed by …

Chemoenzymatic approach to enantiopure streptogramin B variants: characterization of stereoselective pristinamycin I cyclase from Streptomyces pristinaespiralis

C Mahlert, SA Sieber, J Grünewald… - Journal of the American …, 2005 - ACS Publications
Streptogramin B antibiotics are cyclic peptide natural products produced by Streptomyces
species. In combination with the synergistic group A component, they are “last line of …

Guanitrypmycin Biosynthetic Pathways Imply Cytochrome P450 Mediated Regio‐and Stereospecific Guaninyl‐Transfer Reactions

J Liu, X Xie, SM Li - Angewandte Chemie International Edition, 2019 - Wiley Online Library
Mining microbial genomes including those of Streptomyces reveals the presence of a large
number of biosynthetic gene clusters. Unraveling this genetic potential has proved to be a …

[HTML][HTML] A [6+ 4]-cycloaddition adduct is the biosynthetic intermediate in streptoseomycin biosynthesis

KB Wang, W Wang, B Zhang, X Wang, Y Chen… - Nature …, 2021 - nature.com
Abstract Streptoseomycin (STM, 1) is a bacterial macrolactone that has a unique 5/14/10/6/6-
pentacyclic ring with an ether bridge. We have previously identified the biosynthetic gene …

[HTML][HTML] The convergent total synthesis and antibacterial profile of the natural product streptothricin F

MG Dowgiallo, BC Miller, M Kassu, KP Smith… - Chemical …, 2022 - pubs.rsc.org
A convergent, diversity-enabling total synthesis of the natural product streptothricin F has
been achieved. Herein, we describe the potent antimicrobial activity of streptothricin F and …

[HTML][HTML] Identification of (2S,3S)-β-Methyltryptophan as the Real Biosynthetic Intermediate of Antitumor Agent Streptonigrin

D Kong, Y Zou, Z Zhang, F Xu, NL Brock, L Zhang… - Scientific Reports, 2016 - nature.com
Streptonigrin is a potent antitumor antibiotic, active against a wide range of mammalian
tumor cells. It was reported that its biosynthesis relies on (2 S, 3 R)-β-methyltryptophan as an …

Natural Combinatorial Biosynthesis Involving Two Clusters for the Synthesis of Three Pyrrolamides in Streptomyces netropsis

A Vingadassalon, F Lorieux, M Juguet… - ACS Chemical …, 2015 - ACS Publications
The pyrrolamides constitute a small family of secondary metabolites that are known for their
ability to bind noncovalently to the DNA minor groove with some sequence specificity. To …

Studies on the formation and incorporation of streptolidine in the biosynthesis of the peptidyl nucleoside antibiotic streptothricin F

MD Jackson, SJ Gould… - The Journal of Organic …, 2002 - ACS Publications
Streptothricin F (STF, 1) is a peptidyl nucleoside antibiotic produced by Streptomyces
lavendulae. Studies were conducted to address the formation and timing of incorporation of …

Characterization of streptonigrin biosynthesis reveals a cryptic carboxyl methylation and an unusual oxidative cleavage of a N–C bond

F Xu, D Kong, X He, Z Zhang, M Han… - Journal of the …, 2013 - ACS Publications
Streptonigrin (STN, 1) is a highly functionalized aminoquinone alkaloid with broad and
potent antitumor activity. Here, we reported the biosynthetic gene cluster of STN identified by …