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David R. Mootoo, Ph.D.
Professor - Organic Chemistry
Contact Information:
office 1305aN (tel 212-772-4356), lab 1306N (tel 212-650-3718), fax (dept) 212-772-5332, email dmootoo@hunter.cuny.edu
Education:
B.S. & M.S.: University of the West Indies, Ph.D.: University of Maryland, Post-Doctoral Research: Duke University
Research Summary:
Our research centers on the design and synthesis of molecular probes for biological pathways, with the ultimate goal of elucidating disease processes and devising new therapeutic strategies. The underlying synthetic and mechanistic chemistry bear wider relevance to the field of bioorganic chemistry. Our interests span two broad categories of molecules, unnatural analogues of disease-related carbohydrates and structurally related natural products with unique biological activity.
Selected Publications
Glycomimetics
Denton, R. W.; Cheng, X.; Tony, K. A.; Dilhas, A.; Hernández, J. J.; Canales, A.; Jiménez-Barbero, J.; Mootoo, D. R. C-disaccharides as probes for carbohydrate recognition. Investigation of the conformational requirements for binding of disaccharide mimetics of sialyl Lewis X. Eur. J. Org. Chem. 2007, 645-654.
Pérez-Castells, J.; Hernández-Gay, J. J.; Denton, R. W.; Tony, K. A.; Cañada, F. J.; Mootoo, D. R.; Jiménez-Barbero. The conformational behavior and P-selectin inhibition of fluorine containing sialyl Lewis X glycomimetics. Org. Biomol. Chem 2007 5, 1087-1092.
Tony, K. A.; Denton, R. W.; Dilhas, A.; Jiménez-Barbero, J.; Mootoo, D. R. Synthesis of b-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent. Org. Lett. 2007 9, 1441-1444.
Garg, H.; Francella, N.; Tony, K. A.; Augustin, L. A.; Fantini, J.; Barchi Jr, J. J.; Puri, A.; Mootoo, D. R.; Blumenthal, R. Glycoside analogues of b-galactosylceramide, a novel class of small molecule inhibitors for HIV-1 entry. Antiviral Res. 2008 80, 54-61.
Hans, S. K.; Camara, F.; Altiti, A. Martin-Montalvo Sanchez, A.; Brautigan, D. L.; Heimark, D.; Larner, J.; Grindrod, S.; Brown, M. L.; Mootoo, D. R. Synthesis of C-glycoside analogues of b-galactosamine-(1->4)-3-O-methyl-D-chiro-inositol and assay as activator of protein phosphatases PDHP and PP2Ca. Bioorg. Med. Chem. 2010, 18, In press. doi:10.1016/j.bmc.
Natural Products
Li, X.; Li, J.; Mootoo, D. R. Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: An iodoetherification-dehydroiodination strategy for complex spiroketals. Org. Lett. 2007, 9, 4303-4306.
Li, J.; Todaro, L.J.; Mootoo, D. R. Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence. Org. Lett. 2008,10, 1337-1340.
Wang, F.; Kawamura, A. Mootoo, D. R. Synthesis and antitumor activity of C-9 epimers of the tetrahydrofuran containing acetogenin 4-deoxyannoreticuin. Bioorg. Med. Chem. 2008,16, 8413-8418
Tony, K. A.; Li, X.; Dabideen, D.; Li, J.; Mootoo, D. R. An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors. Org. Biomol. Chem., 2008, 6, 1165-1169.
Tony, K. A.; Dabideen, D.; Li, J.; Díaz-Hernández, M. D.; Jiménez-Barbero, J.; Mootoo, D. R. An olefin metathesis-iodoetherification-dehydroiodination strategy for spiroketal subunits of the polyether antibiotics. J. Org. Chem. 2009, 74, 7774–7780.