Streptomycin is an antibiotic active against tuberculosis, and its discovery has become something of a cause célèbre. It was first isolated on October 19, 1943 by a graduate student Albert Schatz in the laboratory of Selman Waksman at Rutgers University. I want to concentrate in this post on its molecular structure. Its initial isolation was followed by an extraordinarily concentrated period of about three years devoted to identifying that structure, culminating in a review of this chemistry in 1948 by Lemieux and Wolfram. This review presents the structure as shown below (left). The modern rendering on the right is based on a crystal structure done in 1978.
- R. Lemieux, and M. Wolfrom, "The Chemistry of Streptomycin", Advances in Carbohydrate Chemistry, pp. 337-384, 1948. http://dx.doi.org/10.1016/S0096-5332(08)60034-X
- S. Neidle, D. Rogers, and M.B. Hursthouse, "The Crystal and Molecular Structure of Streptomycin Oxime Selenate Tetrahydrate", Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, vol. 359, pp. 365-388, 1978. http://dx.doi.org/10.1098/rspa.1978.0047