Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

• Lisa Ziesche,
• Jan Rinkel,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 1309–1316, doi:10.3762/bjoc.14.112

• determined using GC/MS [9][10][32]. Coenzyme A or abbreviated ACP analogs, N-pantothenoylcysteamine thioesters of fatty acids (PCEs) were synthesized (Scheme 2) to serve as substrate substitutes for the native precursors. Calcium pantothenate (6) was protected with acetone forming acid 7 that was transformed

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

• . Remarkably, most coenzymes –necessary effectors of metabolism, the existence of which is a prerequisite for any plausible scenario of origin– are today synthesised from simple carbon molecules and amino acids. Among those, 4′-phosphopantetheine (cysteine condensed with pantothenate, a derivative of valine

A cross-metathesis approach to novel pantothenamide derivatives

• Jinming Guan,
• Matthew Hachey,
• Lekha Puri,
• Vanessa Howieson,
• Kevin J. Saliba and
• Karine Auclair

Beilstein J. Org. Chem. 2016, 12, 963–968, doi:10.3762/bjoc.12.95

• larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood. Keywords: antibiotic; antiplasmodial; coenzyme A; metathesis; pantothenate; Introduction Bacteria, fungi, and parasites are all rapidly acquiring resistance to

• enzymes, the pantetheinases, that normally hydrolyze pantetheine to pantothenate and cysteamine in human blood [10], which precludes their clinical application. The antimicrobial activity of pantothenamides is believed to arise from at least two mechanisms depending on the microbial strain. In E. coli

• pantothenamides may mimic pantetheine and are extended into a thiol-lacking coenzyme A (CoA) derivative by some of the natural CoA biosynthetic enzymes (pantothenate kinase or PanK, phosphopantetheine adenylyltransferase and dephosphocoenzyme A kinase). The resulting inactive CoA analog affects downstream