caa a22 4500 467919704 CHVBK 20180406152913.0 cr unu---uuuuu 170328e20061201xx s 000 0 eng 10.1007/s00706-006-0556-3 doi (NATIONALLICENCE)springer-10.1007/s00706-006-0556-3 Partial Synthesis of CoαCoβ-Dicyano-176-Norcobinamide [Elektronische Daten] [Philip A. Butler, Shahzad Murtaza, Bernhard Kräutler] Summary.: Recent interest in norvitamin B12-derivatives, homologues of complete vitamin B12-derivatives, lacking the methyl group at carbon 176, stems from the identification of the corrinoid cofactor of the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans as 176-nor-pseudovitamin B12. Here we report the partial synthesis of the corrinoid CoαCoβ-dicyano-176-norcobinamide by condensation of cobyric acid and 2-aminoethanol. In addition, the partial synthesis of crystalline Coα-aquo-Coβ-cyanocobyric acid by acid catalyzed hydrolysis of vitamin B12 is detailed, improving the method and the isolation procedure worked out earlier by Bernhauer et al. The solution structure of CoαCoβ-dicyano-176-norcobinamide was studied by spectroscopy and was compared with that of the homologue CoαCoβ-dicyanocobinamide. The title compound, CoαCoβ-dicyano-176-norcobinamide, represents the dicyano-form of a potential biosynthetic precursor of the 176-nor-B12-derivatives, such as 176-nor-pseudovitamin B12. Springer-Verlag, 2006 Keywords. Corrinoid nationallicence Dehalogenase nationallicence Synthesis nationallicence Vitamin B12 nationallicence Butler Philip A. Institut für Organische Chemie & Center of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria aut Murtaza Shahzad Institut für Organische Chemie & Center of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria aut Kräutler Bernhard Institut für Organische Chemie & Center of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/12(2006-12-01), 1579-1589 0026-9247 137:12<1579 2006 137 706 https://doi.org/10.1007/s00706-006-0556-3 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0556-3 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Butler Philip A. Institut für Organische Chemie & Center of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria aut NATIONALLICENCE 700 1- Murtaza Shahzad Institut für Organische Chemie & Center of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria aut NATIONALLICENCE 700 1- Kräutler Bernhard Institut für Organische Chemie & Center of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/12(2006-12-01), 1579-1589 0026-9247 137:12<1579 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer