Creating diverse glycosides of 2′-hydroxyflavone through microbial glycosylation

Ren, Jie; Barton, Caleb Don; Zhan, Jixun

doi:10.1016/j.fitote.2022.105247

Cited by 5 publications

(1 citation statement)

References 28 publications

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“…After extraction with ethyl acetate, a yellow powder of monorhamnosyl NOS (~150 mg) was obtained using semi-preparative HPLC, with the purity exceeding 95%. Further NMR analysis confirmed that the monorhamnosyl NOS was the desired derivative, designated as NOS-R, which possesses an Oα-glycosidic bond at the hydroxyl group of 3-hydroxylpyridine in NOS as compared with NMR data for reported rhamnosyl compounds (Ren et al, 2022; Figure 1 and Table S6). This finding suggests that Streptomyces sp.…”

Section: Structural Identification Of Rhamnosyl Nosmentioning

confidence: 69%

Selective biosynthesis of a rhamnosyl nosiheptide by a novel bacterial rhamnosyltransferase

Du,

Xia,

et al. 2024

Microbial Biotechnology

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Nosiheptide (NOS) is a thiopeptide antibiotic produced by the bacterium Streptomyces actuosus. The hydroxyl group of 3‐hydroxypyridine in NOS has been identified as a promising site for modification, which we therefore aimed to rhamnosylate. After screening, Streptomyces sp. 147326 was found to regioselectively attach a rhamnosyl unit to the 3‐hydroxypyridine site in NOS, resulting in the formation of a derivative named NOS‐R at a productivity of 24.6%. In comparison with NOS, NOS‐R exhibited a 17.6‐fold increase in aqueous solubility and a new protective effect against MRSA infection in mice, while maintaining a similar in vitro activity. Subsequently, SrGT822 was identified as the rhamnosyltransferase in Streptomyces sp. 147326 responsible for the biosynthesis of NOS‐R using dTDP‐L‐rhamnose. SrGT822 demonstrated an optimal reaction pH of 10.0 and temperature of 55°C, which resulted in a NOS‐R yield of 74.9%. Based on the catalytic properties and evolutionary analysis, SrGT822 is anticipated to be a potential rhamnosyltransferase for use in the modification of various complex scaffolds.

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Section: Structural Identification Of Rhamnosyl Nosmentioning

confidence: 69%