We also have had exciting preliminary
results with virus particles covered with the carbohydrates rich in mannose that
make up the defensive coating of the virus that causes AIDS. When we array these
carbohydrates on our innocuous virus carriers, the resulting particles can interfere
with the binding of HIV to an antibody currently known to be protective against
viral infection when present in high concentrations in the body. Our virus-carbohydrate
particles are therefore of interest as potential vaccines, and preliminary experiments
in rabbits are under way in collaboration with D.R. Burton at Scripps Research.
New Chemically Modified Viruses
We have found bacteriophage Qβ is a superior platform for the incorporation of unnatural amino acids and their subsequent derivatization by the azide-alkyne cycloaddition reaction. This particle now forms the basis of the immunization studies previously described, as well as other efforts in the areas of cancer targeting and catalysis.
Dìaz, D.D., Converso, A., Sharpless, K.B., Finn, M.G. 2,6-dichloro-9-thiabicyclo[3.3.1]nonane: multigram display of azides and cyanides components on a versatile scaffold. Molecules 11:212, 2006.
Dìaz, D.D., Finn, M.G., Mishima, M. Substituent effects on the gas-phase basicity of formamidine ureas. Eur. J. Org. Chem. 235, 2006, Issue 1.
Dìaz, D.D., Lewis, W.G., Finn, M.G. Activation of urea as a leaving group in substitution reactions of formamidine ureas. Chem. Lett. 34:78, 2005.
Dìaz, D.D., Rajagopal, K., Strable, E., Schneider, J., Finn, M.G. Click chemistry in a supramolecular environment: stabilization of organogels by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. J. Am. Chem. Soc. 128:6056, 2006.
Dìaz, D.D., Sen Gupta, S., Kuzelka, J., Cymborowski, M., Sabat, M., Finn, M.G. Bis(formamidine-urea) complexes of NiII and CuII: synthesis, characterization, and reactivity. Eur. J. Inorg. Chem. 4489, 2006, Issue 22.
Finn, M.G. Emerging high-throughput screening methods for asymmetric induction. In: Chiral Analysis. Busch, K.W., Busch, M.A. (Eds.). Elsevier, St. Louis, in press.
Johnson, J.A., Lewis, D.R., Dìaz, D.D., Finn, M.G., Koberstein, J.T., Turro, N.J. Synthesis of degradable model networks via ATRP and click chemistry. J. Am. Chem. Soc. 128:6564, 2006.
Li, C., Finn, M.G. Click chemistry in materials synthesis, 2: acid-swellable crosslinked polymers made by copper-catalyzed azide-alkyne cycloaddition. J. Polym. Sci. A Polym. Chem. 44:5513, 2006.
Punna, S., Kaltgrad, E., Finn, M.G. Clickable agarose for affinity chromatography. Bioconjug. Chem. 16:1536, 2005.
Sen Gupta, S., Kuzelka, J., Singh, P., Lewis, W.G., Manchester, M., Finn, M.G. Accelerated bioorthogonal conjugation: a practical method for the ligation of diverse functional molecules to a polyvalent virus scaffold. Bioconjug. Chem. 16:1572, 2005.
Whiting, M., Muldoon, J., Lin, Y.-C., Silverman, S.M., Lindstrom, W., Olson, A.J., Kolb, H.C., Finn, M.G., Sharpless, K.B., Elder, J.H., Fokin, V.V. Inhibitors of HIV-1 protease via in situ click chemistry. Angew. Chem. Int. Ed. 45:1435, 2006.
Wu, P., Malkoch, M., Hunt, J., Vestberg, R., Kaltgrad, E., Finn, M.G., Fokin, V.V., Sharpless, K.B., Hawker, C.J. Multivalent, bifunctional dendrimers prepared by click chemistry. Chem. Commun. (Camb.) 5775, 2005, Issue 46.
Yang, H., Das, N., Huang, F., Hawkridge, A.M., Arif, A.M., Finn, M.G., Muddiman, D.C., Stang, P.J. Incorporation of 2,6-di(4,4′-dipyridyl)-9-thiabicyclo[3.3.1]-nonane into discrete 2D supramolecules via coordination-driven self-assembly. J. Org. Chem. 71:6644, 2006.