Partial synthesis of Co alpha Co beta-dicyano-176-norcobinamide
Butler, PA; Murtaza, S; Kraeutler, B
| HERO ID | 3559352 |
|---|---|
| In Press | No |
| Year | 2006 |
| Title | Partial synthesis of Co alpha Co beta-dicyano-176-norcobinamide |
| Authors | Butler, PA; Murtaza, S; Kraeutler, B |
| Journal | Monatshefte für Chemie / Chemical Monthly |
| Volume | 137 |
| Issue | 12 |
| Page Numbers | 1579-1589 |
| Abstract | Recent interest in norvitamin B-12-derivatives, homologues of complete vitamin B-12-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 B-12. Here we report the partial synthesis of the corrinoid Co alpha Co beta-dicyano-176-norcobinamide by condensation of cobyric acid and 2-aminoethanol. In addition, the partial synthesis of crystalline Co-alpha-aquo-Co-beta-cyanocobyric acid by acid catalyzed hydrolysis of vitamin B-12 is detailed, improving the method and the isolation procedure worked out earlier by Bernhauer et al. The solution structure of Co alpha Co beta-dicyano-176-norcobinamide was studied by spectroscopy and was compared with that of the homologue Co alpha Co beta-dicyanocobinamide. The title compound, Co alpha Co beta-dicyano-176-norcobinamide, represents the dicyano-form of a potential biosynthetic precursor of the 176-nor-B-12-derivatives, such as 176-nor-pseudovitamin B-12. |
| Doi | 10.1007/s00706-006-0556-3 |
| Wosid | WOS:000242660600010 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | corrinoid; dehalogenase; synthesis; vitamin B12 |