Silva Pamela M, Toledo Mônica F Z J, Manarin Flávia, Pimenta Daniel C, Pereira Nicaely M O, Bastos Erick L, da Silva Vinicius M, Hornink Milene M, Stefani Hélio A
Centro Universitário São Camilo, São Paulo, São Paulo 05508-900, Brazil.
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, São Paulo 05508-900, Brazil.
ACS Omega. 2025 Jul 15;10(29):32444-32453. doi: 10.1021/acsomega.5c04865. eCollection 2025 Jul 29.
This study reports on the development of a palladium-catalyzed carbonylative coupling reaction for synthesizing glucal amino acids and fluorescent amino acid derivatives. A metal carbonyl was employed as a CO surrogate, avoiding the use of CO gas. Utilizing Pd-(OAc) and triphenylphosphine, methyl esters of L-amino acids were coupled with 1-iodoglucal under optimized reaction conditions. Yields of up to 65% were achieved. The methodology was applied to amino acids with different side chains. Notably, the synthesized fluorescent derivatives containing stilbene moieties exhibited distinct absorption and emission properties with high fluorescence quantum yields.
本研究报道了一种用于合成葡糖醛酸氨基酸和荧光氨基酸衍生物的钯催化羰基化偶联反应的进展。使用金属羰基化合物作为一氧化碳替代物，避免了使用一氧化碳气体。在优化的反应条件下，利用醋酸钯和三苯基膦，将L-氨基酸甲酯与1-碘葡糖醛酸进行偶联。产率高达65%。该方法适用于不同侧链的氨基酸。值得注意的是，合成的含有芪基部分的荧光衍生物表现出独特的吸收和发射特性，荧光量子产率高。
