Katja Michael
BIOORGANIC CHEMISTRY

Associate Professor
B.A., University of Frankfurt, 1990
Ph.D., Technical University of Munich, 1996
Postdoctoral Fellow, University of California, San Diego 1996-1999

Assistant Professor, University of Hawaii, 2000-2006
Phone:(915) 747-5240

Michael Research Group Site

Awards and Activities
Victoria S. and Bradley L. Geist Foundation, 2001

ACS PRF Type G Award, 2003
NSF award, CHE-0719538, 2007

Research Interests
Synthesis of peptides and proteins with posttranslational modifications. My research focuses primarily on the synthetic method development for the construction of glycopeptides and glycoproteins. Covalent glycosylation occurs in the vast majority of proteins that transit through the endoplasmatic reticulum in eukaryotic cells. These include proteins that remain in the cell, and proteins secreted into the extracellular milieu. The carbohydrate portions have essential biological or structural functions, which are generally not well understood. The availability of structurally well-defined glycopeptides and glycoproteins is essential for the study of glycobiology and proteomics. We have developed a photochemical method that allows for the convergent synthesis of complex N-glycopeptides under neutral reaction conditions by placing a photoreactive group in the side chain of asparagines. We are now extending this research to the development of novel photoreactive solid supports with dual functionality, which enables us to synthesize C-terminally photoreactive peptides which can be derivatized by illumination with UV light in the presence of nucleophiles. For example, in the presence of mercaptans, (glycol) peptide thioesters are generated, which serve as building blocks for the chemical synthesis of (glyco)proteins.

Selected Publications

· Vízvárdi, K.; Kreutz, C.; Davis, A.S.; Lee, V.P.;Philmus, B.J.; Simo, O.; Michael, K. “Phototransamidation as a method for the synthesis of N-glycosyl asparagines”, Chemistry Letters 2003, 32, 348-349.

· Michael, K.; Wang, Q.; Sanki, A.K. “Synthesis of proliferating azido-LacNac derivatives as precursors of a combinatorial divers LacNac library for the generation of potent galectin binders” Glycobiology 2004, 14, abstract 129.

· Simo,O.; Lee, V.P.; Davis, A.S.; Kreutz, C.; Gross,P.H.; Jones, R.P.; Michael, K. “Synthesis of glycosyl amino acids by light-induced coupling of photoreactive amino acids with glycosylamines and 1-C-aminomethyl glycosides, Carbohydrate Research 2005, 340, 557-566.

· Simo, O.; Michael, K.; Yoshida, W.; Chertkov, V.A.; Gross, P.H. “Selective reductions of C-(4,6-O-benzylidene-b-d-glucopyranosyl nitromethane” Synthetic Communications 2005, 35, 1589-1599.

· Kaneshiro, C.M.; Michael, K. “A novel convergent synthesis of N-linked glycopeptides” Angew. Chem. Int. Ed. 2006, 45, 1077-1081.

· Michael, K. “Convergent N-glycopeptide synthesis” in Frontiers in Modern Carbohydrate Chemistry , Ed. Demchenko, A. American Chemical Society, 2007,
p. 328 - 353

· T.J Hogenauer, Q. Wang, A.K. Sanki, A.J. Gammon, C.H.L. Chu, C.M. Kaneshiro, Y. Kajihara, K. Michael "Virtually epimerization-free synthesis of peptide-aLPHA-thioesters" Org. Biomo. Chem. 2007, 5, 759-762.