Kinetics of Strain-Promoted Alkyne-Nitrone Cycloadditions (SPANC) with Unprotected Carbohydrate Scaffolded Nitrones

• DOI: 10.1021/acs.orglett.4c01098
• Publication Date: 2024-05-01T11:50:50Z
• Authors: Nathan Noël; Agathe Martinez; Fabien Massicot; Jean-Luc Vasse; Jean-Bernard Behr
• Keywords: Nitrone; Alkyne; Strain (injury)

The use of unprotected carbohydrate-derived nitrones as partners in strain-promoted alkyne-nitrone cycloadditions was investigated a new tool for bioconjugation. observed second-order reactions displayed rate constants 3.4 × 10-4-5.8 10-2 M-1 s-1, which is the common order magnitude reaction kinetics with other simple aliphatic or aromatic nitrones. Applicability this method to aqueous media demonstrated by performing one-pot protocol, combines sequential formation nitrone and cycloaddition cyclooctyne water.