ArticleChembiochem : a European journal of chemical biology2026
A Streamlined Synthesis of Adenosine Vinylsulfonamide Probes for Aminoacyl-AMP Mimicry in NRPS.
Article in Chembiochem : a European journal of chemical biology, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Adenosine vinylsulfonamide (AVS) probes provide a powerful means of stabilizing the thioesterification state in nonribosomal peptide synthetases (NRPSs) by mimicking aminoacyl-AMP intermediates. Existing synthetic strategies have enabled broad application of this probe class, yet they often rely on strongly basic conditions for constructing the key CC bond from α-amino aldehydes, substrates that are inherently prone to epimerization. These features limit practical access to AVS derivatives from nonproteinogenic amino acids, many of which are central to NRPS-mediated natural product biosynthesis. To address these constraints, we developed a concise three-step route beginning from N-Boc amino alcohols that proceeds under operationally simple and stereochemically controlled conditions. A preassembled adenosine phosphinyl sulfonamide serves as an effective coupling partner in a Ba(OH)
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