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由受细胞色素P450启发的雅各布森催化剂/纤维素体系促进的罗丹明B氧化反应。

Rhodamine B oxidation promoted by P450-bioinspired Jacobsen catalysts/cellulose systems.

作者信息

Bolzon Lucas Bomfim, Bindeiro Anna Karolina Dos Santos, de Oliveira Souza Ana Luiza Marques, Zanatta Lucas Dimarô, de Paula Rodrigo, Cerqueira Bruna Costa, Dos Santos Joicy Santamalvina

机构信息

Grupo de Pesquisa em Bioinorgânica e Catálise (GPBioCat), Departamento de Química Geral e Inorgânica, IQ-UFBA R. Barão de Jeremoabo 147, Campus de Ondina 40170-115 Salvador BA Brazil

Laboratório de Bioinorgânica, Departamento de Química, FFCLRP-USP Av. Bandeirantes 3900 14040-901 Ribeirão Preto SP Brazil.

出版信息

RSC Adv. 2021 Nov 2;11(53):33823-33834. doi: 10.1039/d1ra04915a. eCollection 2021 Oct 8.

DOI:10.1039/d1ra04915a
PMID:35497525
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9042282/
Abstract

In this work, we investigated the preparation of P450-bioinspired Mn(iii)-Schiff base complexes supported on DEAE-cellulose ((,)-Jacobsen/Cell(NEt) and (,)-Jacobsen/Cell(NEt), respectively) to oxidize substrates of biological interest. Catalysts were characterized by several physical techniques. UV-Vis spectroscopy with diffuse reflectance (DR/UV-Vis) analysis featured peculiar electronic transitions for both complexes. Fourier transform infrared (FTIR) spectra evidenced the characteristic band of imine groups (HC[double bond, length as m-dash]N) for bioinspired/Cell(NEt) materials. Immobilization ratios in cellulose fibres were confirmed by atomic absorption spectroscopic (GF-AAS) analyses. Catalytic essays were conducted during rhodamine B (RhB) oxidation. Supported materials attained oxidative yields close to those of homogeneous systems, and cellulose may be stabilizing the active intermediate catalytic species. Reactions may be driven through two different intermediates: Mn(O) and Mn(O-OH)salen. Homogeneous reactions suggest an asymmetric catalysis. Heterogeneous system reaction yields are similar, and salen complexes anchored on cellulose conformation would interfere on complex intermediate species configuration. The four possible RhB-oxidation products obtained by the reaction with the homogeneous (,)-Jacobsen catalyst and -chloroperoxybenzoic acid (-CPBA) system were suggested by H NMR analysis, and a catalytic mechanism was proposed.

摘要

在本工作中，我们研究了负载于二乙氨基乙基纤维素上的受细胞色素P450启发的锰（Ⅲ）-席夫碱配合物（分别为(,)-雅各布森/纤维素(NEt)和(,)-雅各布森/纤维素(NEt)）的制备，用于氧化具有生物学意义的底物。通过多种物理技术对催化剂进行了表征。采用漫反射紫外可见光谱（DR/UV-Vis）分析的紫外可见光谱显示了两种配合物独特的电子跃迁。傅里叶变换红外光谱（FTIR）证明了受生物启发的/纤维素(NEt)材料中亚胺基团（HC[双键，长度为m破折号]N）的特征谱带。通过原子吸收光谱（GF-AAS）分析确定了纤维素纤维中的固定化比率。在罗丹明B（RhB）氧化过程中进行了催化实验。负载材料的氧化产率接近均相体系，并且纤维素可能稳定了活性中间催化物种。反应可能通过两种不同的中间体进行：Mn（O）和Mn（O-OH）席夫碱。均相反应表明存在不对称催化。非均相体系的反应产率相似，并且固定在纤维素构象上的席夫碱配合物会干扰复杂中间物种的构型。通过与均相(,)-雅各布森催化剂和-氯过氧苯甲酸（-CPBA）体系反应得到的四种可能的RhB氧化产物通过核磁共振氢谱分析得到提示，并提出了催化机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/108818f859aa/d1ra04915a-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/150dcb66cf1f/d1ra04915a-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/5e1c09d4e1b6/d1ra04915a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/081108d2c7e8/d1ra04915a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/961be0e5ad59/d1ra04915a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/496cad4dcd23/d1ra04915a-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/31d4d91cb2ad/d1ra04915a-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/108818f859aa/d1ra04915a-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/150dcb66cf1f/d1ra04915a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/f21a1fe8049b/d1ra04915a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/cc04bc9b017b/d1ra04915a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/5e1c09d4e1b6/d1ra04915a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/081108d2c7e8/d1ra04915a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/961be0e5ad59/d1ra04915a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/496cad4dcd23/d1ra04915a-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/31d4d91cb2ad/d1ra04915a-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6423/9042282/108818f859aa/d1ra04915a-f9.jpg

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