Noël Nathan, Martinez Agathe, Massicot Fabien, Vasse Jean-Luc, Behr Jean-Bernard
Université de Reims Champagne-Ardenne, CNRS UMR 7312, ICMR, 51687 Reims, France.
Org Lett. 2024 May 10;26(18):3917-3922. doi: 10.1021/acs.orglett.4c01098. Epub 2024 May 1.
The use of unprotected carbohydrate-derived nitrones as partners in strain-promoted alkyne-nitrone cycloadditions was investigated as a new tool for bioconjugation. The observed second-order reactions displayed rate constants of 3.4 × 10-5.8 × 10 M s, which is the common order of magnitude of reaction kinetics with other simple aliphatic or aromatic nitrones. Applicability of this method to aqueous media was demonstrated by performing a one-pot protocol, which combines sequential formation of the nitrone and cycloaddition with cyclooctyne in water.
研究了使用未受保护的碳水化合物衍生的硝酮作为应变促进的炔-硝酮环加成反应中的伙伴，作为生物共轭的一种新工具。观察到的二级反应显示速率常数为3.4×10 - 5.8×10 M s，这与其他简单脂肪族或芳香族硝酮的反应动力学的常见数量级相同。通过执行一锅法方案证明了该方法在水性介质中的适用性，该方案将硝酮的顺序形成以及与环辛炔在水中的环加成反应结合在一起。
