Nitrite increases the enantioselectivity of sulfoxidation catalyzed by myoglobin derivatives in the presence of hydrogen peroxide

被引：6
|
作者：
Pironti, V
Nicolis, S
Monzani, E
Colonna, S
Casella, L
机构：
[1] Univ Pavia, Dipartimento Chim Gen, I-27100 Pavia, Italy
[2] Univ Milan, Ist Chim Organ Alessandro Marchesini, Fac Farm, I-20133 Milan, Italy
来源：
TETRAHEDRON | 2004年 / 60卷 / 37期
关键词：
asymmetric oxidation; myoglobin; nitrite; NMR; sulfoxidation;
D O I：
10.1016/j.tet.2004.06.097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The effect of nitrite in the sulfoxidation of organic sulfides catalyzed by myoglobin (Mb) in the presence of hydrogen peroxide has been investigated. A general improvement in enantioselectivity was found for the reaction catalyzed by horse heart metMb and a series of sperm whale metMb derivatives including the wild type protein, the active site mutants T67K Mb, T67R Mb, T67R/S92D Mb, and the T67K Mb derivative reconstituted with the modified prosthetic group protohemin-L- histidine methyl ester. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8153 / 8160
页数：8
相关论文
共 50 条
  • [1] Mechanistic insight into the peroxidase catalyzed nitration of tyrosine derivatives by nitrite and hydrogen peroxide
    Monzani, E
    Roncone, R
    Galliano, M
    Koppenol, WH
    Casella, L
    EUROPEAN JOURNAL OF BIOCHEMISTRY, 2004, 271 (05): : 895 - 906
  • [2] Easy oxidation and nitration of human myoglobin by nitrite and hydrogen peroxide
    Nicolis, S
    Pennati, A
    Perani, E
    Monzani, E
    Sanangelantoni, AM
    Casella, L
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) : 749 - 757
  • [3] Oxidation of thiamine on reaction with nitrogen dioxide generated by ferric myoglobin and hemoglobin in the presence of nitrite and hydrogen peroxide
    Stepuro, I. I.
    Oparin, A. Yu
    Stsiapura, V. I.
    Maskevich, S. A.
    Titov, V. Yu
    BIOCHEMISTRY-MOSCOW, 2012, 77 (01) : 41 - 55
  • [4] Oxidation of thiamine on reaction with nitrogen dioxide generated by ferric myoglobin and hemoglobin in the presence of nitrite and hydrogen peroxide
    I. I. Stepuro
    A. Yu. Oparin
    V. I. Stsiapura
    S. A. Maskevich
    V. Yu. Titov
    Biochemistry (Moscow), 2012, 77 : 41 - 55
  • [5] Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide
    Srour, Hassan
    Le Maux, Paul
    Chevance, Soizic
    Simonneaux, Gerard
    COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) : 3030 - 3050
  • [6] Efficient sulfoxidation with hydrogen peroxide catalyzed by a divanadium-substituted phosphotungstate
    Yamaura, Taiyo
    Kamata, Keigo
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    CATALYSIS TODAY, 2013, 203 : 76 - 80
  • [7] Ti(salen)-catalyzed enantioselective sulfoxidation using hydrogen peroxide as a terminal oxidant
    Saito, B
    Katsuki, T
    TETRAHEDRON LETTERS, 2001, 42 (23) : 3873 - 3876
  • [8] Vanadium-catalyzed enantioselective sulfoxidation of methyl aryl sulfides with hydrogen peroxide as terminal oxidant
    Ohta, C
    Shimizu, H
    Kondo, A
    Katsuki, T
    SYNLETT, 2002, (01) : 161 - 163
  • [9] Chiral N,N′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide
    Wang, Fang
    Feng, Lili
    Dong, Shunxi
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2020, 56 (21) : 3233 - 3236
  • [10] Metmyoglobin-catalyzed exogenous and endogenous tyrosine nitration by nitrite and hydrogen peroxide
    Nicolis, S
    Monzani, E
    Roncone, R
    Gianelli, L
    Casella, L
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (09) : 2281 - 2290
12345