优化的三嗪介导的酰胺化反应，用于透明质酸的高效和可控功能化。
Optimized triazine-mediated amidation for efficient and controlled functionalization of hyaluronic acid.
机构信息
Laboratory of Polymer Chemistry, Department of Chemistry, P.O. Box 55, 00014 University of Helsinki, Finland.
Laboratory of Polymer Chemistry, Department of Chemistry, P.O. Box 55, 00014 University of Helsinki, Finland; Faculty of Pharmacy and Department of Chemistry, Universite de Montreal, CP 6128 Succursale Centre Ville, Montreal, QC H3C 3J7, Canada; World Premier International (WPI) Research Center Initiative, International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan.
出版信息
Carbohydr Polym. 2015 Feb 13;116:42-50. doi: 10.1016/j.carbpol.2014.04.012. Epub 2014 Apr 19.
Triazine-based coupling agents have the potential to replace carbodiimides in the functionalization of hyaluronic acid (HA) giving derivatives with high degrees of substitution (DS) under mild conditions with excellent efficiency. Kinetics of the triazine-mediated amidation of HA in aqueous solution were investigated to understand the reaction mechanism and the role of the amine reagent. The DS decreased with increasing basicity of the amine. The water soluble coupling agent was stable under the reaction conditions (t1/2=10 days) in the absence of amines. The activation of HA proceeded quantitatively. The stoichiometry of amine was the limiting factor in the substitution. Functional HA derivatives with DS up to 55% were obtained by the triazine-mediated amidation. They were used successfully to prepare well-defined HA conjugates via the maleimide-thiol and the azide-alkyne "click" reactions.
基于三嗪的偶联剂有可能在透明质酸（HA）的功能化中替代碳二亚胺，在温和条件下以高取代度（DS）、极好的效率得到衍生物。研究了三嗪介导的水溶液中 HA 的酰亚胺化反应动力学，以了解反应机制和胺试剂的作用。随着胺碱性的增加，DS 降低。水溶性偶联剂在没有胺的情况下在反应条件下稳定（t1/2=10 天）。HA 的活化是定量进行的。胺的化学计量是取代的限制因素。通过三嗪介导的酰亚胺化可以得到 DS 高达 55%的功能化 HA 衍生物。它们成功地用于通过马来酰亚胺-巯基和叠氮化物-炔烃“点击”反应制备定义明确的 HA 缀合物。
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