Vitamin B12 catalysed reactions

被引:260
作者
Giedyk, Maciej [1 ]
Goliszewska, Katarzyna [1 ,2 ]
Gryko, Dorota [1 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
[2] Warsaw Univ Technol, Fac Chem, PL-00664 Warsaw, Poland
关键词
REDUCTIVE DECHLORINATION; HYDROPHOBIC VITAMIN-B-12; ELECTROCHEMICAL REACTIONS; COBALAMIN; DEHALOGENATION; DERIVATIVES; MICROEMULSIONS; GENERATION; ELECTRODES; COMPLEXES;
D O I
10.1039/c5cs00165j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Vitamin B-12 (cobalamin, 1) is one of a few naturally occurring organometallic molecules. As a cofactor for adenosylcobalamin-dependent and methylcobalamin-dependent enzymes, it plays a crucial role in biological processes, including DNA synthesis and regulation, nervous system function, red blood cell formation, etc. Enzymatic reactions, such as isomerisation, dehalogenation, and methyl transfer, rely on the formation and cleavage of the Co-C bond. Because it is a natural, nontoxic, environmentally benign cobalt complex, cobalamin (1) has been successfully utilised in organic synthesis as a catalyst for Co-mediated reactions. This tutorial review concisely describes cobalamin-catalysed organic reactions that hold promise for environmentally friendly cobalt catalysis, leaving the reader with basic knowledge and the ability to harness the catalytic potential of this fascinating molecule.
引用
收藏
页码:3391 / 3404
页数:14
相关论文
共 54 条
[1]   Enhanced reductive dechlorination of tetrachloroethene during reduction of cobalamin (III) by nano-mackinawite [J].
Amir, Amnorzahira ;
Lee, Woojin .
JOURNAL OF HAZARDOUS MATERIALS, 2012, 235 :359-366
[2]   Role of protonation and of axial ligands in the reductive dechlorination of alkyl chlorides by vitamin B12 complexes.: Reductive cleavage of chloroacetonitrile by Co(I) cobalamins and cobinamides [J].
Argüello, JE ;
Costentin, C ;
Griveau, S ;
Savéant, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (14) :5049-5055
[3]   Modification of mesoporous TiO2 electrodes with cross-linkable B12 derivatives [J].
Asaftei, Simona ;
Walder, Lorenz .
LANGMUIR, 2006, 22 (13) :5544-5547
[4]   ELECTRON-TRANSFER .71. REDUCTIONS OF INORGANIC COBALT(III) COMPLEXES BY VITAMIN-B12R (COB(II)ALAMIN) [J].
BALASUBRAMANIAN, PN ;
GOULD, ES .
INORGANIC CHEMISTRY, 1985, 24 (12) :1791-1793
[5]   The many faces of vitamin B12:: Catalysis by cobalamin-dependent enzymes [J].
Banerjee, R ;
Ragsdale, SW .
ANNUAL REVIEW OF BIOCHEMISTRY, 2003, 72 :209-247
[6]   Chemistry and enzymology of vitamin B12 [J].
Brown, KL .
CHEMICAL REVIEWS, 2005, 105 (06) :2075-2149
[7]   VITAMIN-B-12-CATALYZED C,C-BOND FORMATION - SYNTHESIS OF JASMONATES VIA SEQUENTIAL RADICAL REACTION [J].
BUSATO, S ;
SCHEFFOLD, R .
HELVETICA CHIMICA ACTA, 1994, 77 (01) :92-99
[8]   Vitamin B12 derivatives as natural asymmetric catalysts:: Enantioselective cyclopropanation of alkenes [J].
Chen, Y ;
Zhang, XP .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2431-2435
[9]   Comparative study of reaction of cobalamin and cobinamide with thiocyanate [J].
Dereven'kov, Ilia A. ;
Salnikov, Denis S. ;
Makarov, Sergei V. ;
Surducan, Mihai ;
Silaghi-Dumitrescu, Radu ;
Boss, Gerry R. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2013, 125 :32-39
[10]   'Carbene Radicals' in CoII(por)-Catalyzed Olefin Cyclopropanation [J].
Dzik, Wojciech I. ;
Xu, Xue ;
Zhang, X. Peter ;
Reek, Joost N. H. ;
de Bruin, Bas .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) :10891-10902