No crystal structure of metallobleomycin (BLM) exists, and the exact coordination mode of the ligand is unknown. To date, spectroscopic investigations of BLM complexes and crystal structures of BLM models have been used to propose its metal coordination sites. This has led to contradictory interpretations of the metal coordination sphere in BLM. Inorganic molecular mechanics and configurational/conformational searches were used to analyze HOO-CoBLM A2, H2O-CoBLM A2, and HOO-CoPEP with commonly proposed binding geometries. The lowest energy binding geometry found was one with the mannose carbamoyl bound to the cobalt ion. The Monte Carlo dihedral and translational variational searches were able to find most of the configurations available to cobalt(III) bleomycin in the three binding geometries examined.