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首页> 外文会议>Synthetic and mechanistic organic electron transfer reactions >An Electrocatalytic System that Mimics the Catalytic Oxidation of Biogenic Mono- and Polyamines by Semicarbazide-Sensitive Amine Oxidases (SSAOs)
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An Electrocatalytic System that Mimics the Catalytic Oxidation of Biogenic Mono- and Polyamines by Semicarbazide-Sensitive Amine Oxidases (SSAOs)

机译：电催化体系，可模拟氨基脲敏感的氨基氧化酶（SSAO）对生物单胺和多胺的催化氧化

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摘要

Chemoselective oxidation of primary aliphatic biogenic mono-and polyamines into imines has been successfully achieved, under metal-free conditions, by using an electrocatalytic system that mimics the activity of semicarbazide-sensitive amine oxidase (SSAO) enzymes. Accordingly, high catalytic performance was observed with unbranched primary amines such as methylamine and aminoacetone, and with the primary amino groups of diamines and polyamines like putrescine and spermidine, all of them being reference substrates for SSAO enzymes. Furthermore, contrary to flavin-adenine dinucleotide (FAD)-dependent amine oxidase enzymes, no activity was found with secondary and tertiary amines. Finally, when compared with the direct electrochemical oxidation of primary aliphatic amines, which occurs at high anodic potential (E_an > + 1.5 V vs SCE) and led to unstable cation radicals that rapidly deprotonate and attach to the electrode surface (Pt, carbon), 1.0 V was gained using this electrocatalytic process (E_an = + 0.5 V vs SCE).
机译：在无金属条件下，通过使用模仿氨基脲敏感的胺氧化酶（SSAO）酶活性的电催化系统，已成功实现了将初级脂肪族生物单胺和多胺化学选择性氧化成亚胺的作用。因此，在直链伯胺如甲胺和氨基丙酮，以及二胺和多胺的伯氨基如腐胺和亚精胺中均观察到高催化性能，它们都是SSAO酶的参考底物。此外，与黄素腺嘌呤二核苷酸（FAD）依赖的胺氧化酶相反，仲胺和叔胺没有活性。最后，与伯脂肪胺的直接电化学氧化相比，后者在高阳极电势下发生（E_an> + 1.5 V vs SCE），并导致不稳定的阳离子自由基迅速去质子化并附着在电极表面（铂，碳），使用该电催化过程获得1.0 V（E_an = + 0.5 V vs SCE）。

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