α-芳基-α-重氮酰胺的两步合成作为模块化生物可逆标签。
Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels.
机构信息
Department of Chemistry and Koch Institute for Integrative Cancer Research at MIT, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
出版信息
Org Lett. 2021 Apr 16;23(8):3110-3114. doi: 10.1021/acs.orglett.1c00793. Epub 2021 Apr 5.
Abstract
α-Aryl-α-diazoamides were synthesized in two steps under mild conditions. This expeditious route employs Pd-catalyzed C-H arylation of -succinimidyl 2-diazoacetate to obtain -succinimidyl 2-aryl-2-diazoacetates, followed by aminolysis. The ensuing diazo compounds can esterify carboxyl groups in aqueous solution, and the ester products are substrates for an esterase. The broad scope of the synthetic route enables the continued development of diazo compounds in chemical biology.
摘要
α-芳基-α-重氮酰胺在温和条件下经两步合成。这条快捷路线采用 Pd 催化的琥珀酰亚胺 2-重氮乙酸酯的 C-H 芳基化反应，得到琥珀酰亚胺 2-芳基-2-重氮乙酸酯，然后进行氨解。所得重氮化合物可以在水溶液中酯化羧基，酯产物是酯酶的底物。这条合成路线具有广泛的应用范围，为化学生物学中重氮化合物的进一步发展提供了可能。
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