Application of Acyl-S-acetylcysteamine (Acyl-SNAC) thiosters as synthetic mimic in biosynthetic intermediates acyl- CoAs Saad Alrashdi 1,2 , Hai Deng 2 1 University of Aberdeen, Saudi Arabia and 2 University of Aberdeen, UK Acyl-CoAs are a family of metabolic intermediates comprised of an acyl group linked by a thioester bond to coenzyme A. Acyl- S -(N-acetyl) cysteamines (Acyl-SNACs) are synthetic mimics of Acyl-CoAs and have many applications including their using in the biosynthetic studies of natural products and their derivatives 1 . Acyl-SNAC compounds are synthesized as crucial thioester intermediates to probe the biosynthetic enzymes identified for the pathways of natural products, for example, carbazoles and siderophores 2 . Siderophores are produced by microorganisms to scavenge iron from the environment, thereby making this essential metal nutrient available to the microbe. More than 500 siderophores are known to date, but only two were identified to be aryl-containing hydroxamate siderophores, legonoxamines A and B from Streptomyces sp. MA37 2 . In this study, several synthesized SNACs thioester compounds were used to demonstrate that LgoC in the biosynthetic pathway of legonoxamines from Streptomyces sp. MA37 is responsible for the key aryl-hydroxamate forming step. Biochemical characterization found that LgoC displays considerable promiscuity for the acylation between N-hydroxy-cadaverine and SNAC (N-acetylcysteamines) thioester derivatives 2 . References 1. Maglangit F, Tong MH, Jaspars M, Kyeremeh K, Deng H. Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37. Tetrahedron Lett. 2019;60(1):75-79. doi:10.1016/j.tetlet.2018.11.063 2. Maglangit F, Alrashdi S, Renault J, et al. Characterization of the promiscuous: N-Acyl CoA transferase, LgoC, in legonoxamine biosynthesis. Org Biomol Chem. 2020;18(12):2219-2222. doi:10.1039/d0ob00320d
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