摘要
合成金属卟啉作为细胞色素P450的仿酶模拟物已广泛研究,基于酶的高选择催化活性,不同取代卟啉模式在其催化活性方面表现各异。本文提出一个通用、温和的方法用于合成Trans-AB位阻卟啉,在80%的乙醇水溶液中通过盐酸催化芳醛与10-五氟苯基四吡咯烷缩合生成卟啉原,然后氯仿萃取,四氯苯醌氧化合成Trans-AB位阻卟啉,这些合成的卟啉结构上具有在5位固定一个强吸电子基团五氟苯基、15位引入立体位阻芳基,以及提高卟啉的氧化还原电位能力与抑制卟啉的自身堆积问题的特征,并合成获得6个未见文献报道的Trans-AB位阻卟啉,通过核磁氢谱、核磁碳谱、核磁氟谱和高分辨质谱确证了该化合物结构。
Syntheticmetalloporphyrins have been widely studied as bioinspired models of cytochrome P-450(hemoproteins).Owing to the high selectivity of enzyme, different substituted porphyrin modes have exhibited different catalytic activities.In this paper, a general and mild protocol to synthesis of Trans-AB steric porphyrin was developed.In 80% aqueous ethanol by acid-catalyzed(HCl) condensation of aromatic aldehydes with 10-pentafluorophenyl bilane at room temperature to give porphyrinogen, following CHCl_(3)extraction and via TCQ oxidation in sequence.In order to improve the redox potential of porphyrins and inhibit the self-accumulation of porphyrins, Trans-AB porphyrin have been designed and synthesized, which bearing up to a strong electron-withdrawing groups pentafluorophenyl on 5 position, and a bulky steric aryl on 15 position.The structures of six Trans-AB porphyrins were identified by^(1)H-NMR,^(13)C-NMR,^(19)F-NMR and HRMS.
作者
闫晓旺
马晓伟
顾承志
YAN Xiaowang;MA Xiaowei;GU Chengzhi(Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan/School of Chemistry and Chemical Engineering,Shihezi University,Shihezi,Xinjiang 832003,China)
出处
《石河子大学学报（自然科学版）》
CAS
北大核心
2022年第1期7-12,共6页
Journal of Shihezi University(Natural Science)
基金
国家自然科学基金(21463022)
石河子大学创新发展专项(CXFZ202009)。
