The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5715 - 5725
Published: April 9, 2024
Some bacteria produce "bacterial polyynes" bearing a conjugated C≡C bond that starts with terminal alkyne. Ergoynes A and B have been reported as sulfur-containing metabolites from Gynuella sunshinyii YC6258. These compounds were thought to be formed by cycloaddition between bacterial polyyne (named Gs-polyyne) l-ergothioneine. The biosynthetic gene clusters (BGCs), which may contribute their synthesis, present in the YC6258 genome. origin of Gs-polyyne is interesting considering its rare 2-isopentyl fatty acyl skeleton. Here, structures biosynthesis ergoynes verified analytical, chemical, genetic techniques. In extract, was prepared instability, detected major LC peak, not detected. NMR data isolated contradicted proposed structure identified it previously protegenin A. expression BGC Escherichia coli BL21(DE3) also yielded cyclization l-ergothioneine did proceed during sample preparation; base, such potassium carbonate, required. Overall, A, while determined artifacts. This provide derivatization stabilize polyynes or create new chemical space.
Language: Английский