Chloroperoxidase-catalyzed oxidation of methionine derivatives

被引:16
|
作者
Holland, HL [1 ]
Brown, FM [1 ]
Lozada, D [1 ]
Mayne, B [1 ]
Szerminski, WR [1 ]
van Vliet, AJ [1 ]
机构
[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
关键词
amino acid oxidation; biocatalysis; biotransformation; chloroperoxidase; enzyme catalysis; lipase; sulfoxidation;
D O I
10.1139/V02-025
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of N-methoxycarbonyl C-carboxylate ester derivatives of L- and D-methionine and L-ethionine by chloroperoxidase-hydrogen peroxide resulted in oxidation at sulfur to produce the (R-S) sulfoxide in moderate to high diastereomeric excess. The (R-S) sulfoxide of methionine was also obtained in moderate to high diastereomeric excess from (+/-)(SO)-N-methoxycarbonyl-L-methionine methyl ester sulfoxide by ester hydrolysis using alpha-chymotrypsin, Aspergillus sp. protease or subtilisin Carlsberg.
引用
收藏
页码:633 / 639
页数:7
相关论文
共 50 条
  • [21] THE CHLOROPEROXIDASE-CATALYZED OXIDATION OF PHENOLS - MECHANISM, SELECTIVITY, AND CHARACTERIZATION OF ENZYME-SUBSTRATE COMPLEXES
    CASELLA, L
    POLI, S
    GULLOTTI, M
    SELVAGGINI, C
    BERINGHELLI, T
    MARCHESINI, A
    BIOCHEMISTRY, 1994, 33 (21) : 6377 - 6386
  • [22] Chloroperoxidase-catalyzed enantioselective oxidations in hydrophobic organic media
    van de Velde, F
    Bakker, M
    van Rantwijk, F
    Sheldon, RA
    BIOTECHNOLOGY AND BIOENGINEERING, 2001, 72 (05) : 523 - 529
  • [23] Insight into the structural basis of the enantiospecificity of chloroperoxidase-catalyzed epoxidation
    Morozov, Alexander N.
    D'Cunha, Cassian
    Chatfield, David C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [24] THE MECHANISM OF CHLOROPEROXIDASE-CATALYZED N-DEMETHYLATION REACTIONS
    KEDDERIS, GL
    HOLLENBERG, PF
    FEDERATION PROCEEDINGS, 1982, 41 (03) : 745 - 745
  • [25] Chloroperoxidase-catalyzed oxidation of 4,6-dimethyldibenzothiophene as dimer complexes: Evidence for kinetic cooperativity
    Torres, E
    Aburto, J
    ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2005, 437 (02) : 224 - 232
  • [26] Chloroperoxidase-catalyzed epoxidation of styrene in aqueous and nonaqueous media
    Santhanam, L
    Dordick, JS
    BIOCATALYSIS AND BIOTRANSFORMATION, 2002, 20 (04) : 265 - 274
  • [27] Visible light-driven and chloroperoxidase-catalyzed oxygenation reactions
    Perez, Daniel I.
    Grau, Maria Mifsud
    Arends, Isabel W. C. E.
    Hollmann, Frank
    CHEMICAL COMMUNICATIONS, 2009, (44) : 6848 - 6850
  • [28] Hypersensitive radical probe studies of chloroperoxidase-catalyzed hydroxylation reactions
    Toy, PH
    Newcomb, M
    Hager, LP
    CHEMICAL RESEARCH IN TOXICOLOGY, 1998, 11 (07) : 816 - 823
  • [30] Chloroperoxidase-catalyzed asymmetric synthesis of a series of aromatic cyclic sulfoxides
    Allenmark, SG
    Andersson, MA
    TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 1089 - 1094