Abstract
AbstractThe structure of a derivative of coenzyme F430 from methanogenic bacteria, the bromide salt of 12,13‐diepi‐F430 pentamethyl ester (5, X = Br), was determined by X‐ray structure analysis. It reveals a more pronounced saddle‐shaped out‐of‐plane deformation of the macrocycle than any hydroporphinoid Ni complex investigated so far. The crystal structure confirms the constitution proposed for coenzyme F430 (2) and shows that in the epimer 5, the three stereogenic centers in ring D, C(17), C(18), and C(19), have the (17S)‐, (18S)‐, and (19R)‐configuration, respectively. Deuteration and 2D‐NMR studies independently demonstrate that native coenzyme F430 (2) has the same configuration in ring D as the epimer 5. Therefore, our original tentative assignment of configuration at C(19) and C(18) [1] has to be reversed. This completes the assignment of configuration for all stereogenic centers in coenzyme F430, which has the structure shown in Formula 2.
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