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Vitamin B 12 Catalysis: Probing the Structure/Efficacy Relationship
Author(s) -
Karczewski Maksymilian,
Ociepa Michał,
Pluta Katarzyna,
ó Proinsias Keith,
Gryko Dorota
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201606059
Subject(s) - corrin , catalysis , yield (engineering) , chemistry , selectivity , cofactor , ethyl diazoacetate , cyclic voltammetry , vitamin c , combinatorial chemistry , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , enzyme , ring (chemistry) , electrochemistry , cyclopropanation , materials science , biochemistry , electrode , metallurgy
Vitamin B 12 is a cofactor for many enzymes, but it also functions as a catalyst in C−C bond‐forming reactions. Herein, the impact of corrin structural modifications on their catalytic efficacy was examined. Derivatives with various substituents at c ‐, d ‐, and meso ‐positions were synthesised by using traditional and new microwave methodologies, and then tested in the model reaction of 1,1‐diphenylethylene with ethyl diazoacetate. To complement the experimental data, cyclic voltammetry and DFT calculations were performed. Mainly alterations at the c ‐ or d ‐positions influence both the reaction yield and selectivity.