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Education:

• A.B. Biology Carroll College
• M.S. 1955 Bacteriology Montana State University
• Ph.D. 1958 Microbiology University of Wisconsin

Overview

Charles (Professor, Pharmaceutical Sciences and Department of Chemistry) received his A.B.-Biology from Carroll College, M.S. degree in bacteriology from Montana State University in 1955, and his Ph.D. in microbiology from the University of Wisconsin in 1958. He then joined the Squibb Institute for Medical Research as a senior microbial biochemist before returning to Wisconsin in 1960. His research interests include enzymatic catalyses to prepare enantiomerically-pure compounds; total synthesis of natural products; biosynthesis of vancomycin; and enzymatic mechanism of thyroxine biosynthesis.

In recent years, interest in the use of enzymes as chiral catalysts has risen rapidly, because enzymes can exert unique control over several stereochemical aspects in single step reactions, thereby enabling asymmetric transformation to be achieved that cannot currently be matched by non-enzymic catalysts. Our interest is in developing the principles and strategies, so that enzymes may be used routinely as organic chiral reagents. Current projects include the chemoenzymatic synthesis of cryptophycins, a class of potent antitumor agents; the chemoenzymatic synthesis of cyclic-ADP-ribose-phosphate and analogs, which are inducers of calcium release; the isolation and characterization of cyclic-ADP-ribose-phosphate receptors; chemoenzymatic synthesis of vancomycin; and the enzymatic mechanism of thyroid hormone formation.

Work-Related Interests/Research:

Enzymatic catalyses to prepare enantiomerically-pure compounds; total synthesis of natural products; biosynthesis of vancomycin; and enzymatic mechanism of thyroxine biosynthesis

Highlighted Publications:

• G.M. Salamonczyk, K. Han, Z.W. Guo and C.J. Sih, "Total synthesis of cryptophycins via a chemoenzymatic approach," J. Org. Chem., 61, 6893 (1996).
• C.J. Sih, "Chemoenzymatic synthesis of the side chain of taxol," in Enantioselective Synthesis of b-Amino Acids, E. Juaristi (ed.), Wiley-VCH, New York, p. 433, 1997.
• Z.W. Guo, G.M. Salamonczyk, K. Han, K. Machiya and C.J. Sih, "Enzymatic oxidative phenolic coupling," J. Org. Chem., 62, 6700 (1997).
• V.B. Oza, G.M. Salamonczyk, Z.W. Guo and C.J. Sih, "Model reactions of thyroxine biosynthesis. Identification of the key intermediate in thyroxine formation from 3,5-diiodo-L-thyrosine and 4-hydroxy-3,5-diiodophenylpyruvic acid," J. Am. Chem. Soc., 119, 11315 (1997).
• Z.W. Guo, K. Machiya, G.M. Salamonczyk and C.J. Sih, "Total synthesis of bastadins 2, 3 and 6," J. Org. Chem., 63, 4269 (1998).