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Existing synthetic strategies have enabled broad application of this probe class, yet they often rely on strongly basic conditions for constructing the key C\uf8ffC bond from \u03b1\u2010amino 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\u2010mediated natural product biosynthesis. To address these constraints, we developed a concise three\u2010step route beginning from\n                    <jats:italic>N<\/jats:italic>\n                    \u2010Boc 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)\n                    <jats:sub>2<\/jats:sub>\n                    \u2010mediated Horner reaction performed near 0\u00b0C, enabling highly diastereoselective AVS formation with minimal epimerization under mild, open\u2010air conditions. The method tolerates diverse amino acid\u2010derived substrates, including electron\u2010rich L\u2010Tyr derivatives relevant to tetrahydroisoquinoline alkaloid biosynthesis. Functional evaluation by LC\u2013MS\/MS confirmed covalent capture of the NRPS SfmC by an L\u2010Tyr\u2010derived probe, demonstrating that AVS constructs prepared by this route retain full biochemical competence. This streamlined synthesis enhances reliable access to stereochemically well\u2010defined AVS probes and supports structural and mechanistic studies across diverse NRPS systems.\n                  <\/jats:p>","DOI":"10.1002\/cbic.70275","type":"journal-article","created":{"date-parts":[[2026,4,13]],"date-time":"2026-04-13T09:51:16Z","timestamp":1776073876000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["A Streamlined Synthesis of Adenosine Vinylsulfonamide Probes for Aminoacyl\u2010AMP Mimicry in NRPS"],"prefix":"10.1002","volume":"27","author":[{"given":"Naoto","family":"Haraguchi","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science The University of Tokyo  Bunkyo\u2010ku Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arisa","family":"Suto","sequence":"additional","affiliation":[{"name":"Department of Physics School of Science Kitasato University 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