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. 2014 Aug 27;53(41):10925–10927. doi: 10.1002/anie.201406125

Figure 2.

Figure 2

A crystal structure of BBOX complexed with N,N-dimethyl piperidine (1), NiII (as a substitute for FeII), and NOG (N-oxyalyl glycine, a non-reactive 2OG mimetic). A) The view from the active site of the BBOX 1 NiII NOG complex (PDB ID: 4CWD) reveals that 1 adopts a chair conformation, with its pro(R) hydrogen atom, which is hydroxylated, pointing towards the metal. B) An overlay of the active sites of BBOX complexed with GBB, ZnII, and NOG (blue, PDB ID: 3O2G) or with 1, NiII, and NOG (orange, PDB ID: 4CWD) reveal similar positions of the active-site residues and NOG. The carboxylate groups of GBB and 1 are similarly positioned, both interacting with the side chains of Asn191 and Asn292. The quaternary ammonium groups of both GBB and 1 occupy an identical aromatic cage formed by Tyr177, Tyr194, Tyr205, and Trp181. M=metal. Note: the carbons that undergo hydroxylation (C3 in both GBB and 1) are near identically positioned relative to the metal ion in both structures.