Contact Information:

office 1400dNN (tel 212-772-5340), dept fax 212-772-5332, email rfranck@hunter.cuny.edu, group webpage Franck Group Homepage

The Franck lab is not accepting applications for research positions.

Education:

A.B.:Amherst College, M.S.: University of Wisconsin, Ph.D.: Stanford University, Postdoc: Massachusetts Institute of Technology

Research Summary: 

The last challenge in our lab before it shut down in January 2007 was the synthesis of the C-glycoside (C-galcer) analog of a powerful immunostimulant O- glycoside (O-galcer), originally found in a sponge off the coast of Okinawa, shown below. The "replacement" of the -O-link most commonly found in glycosides by -C- is a popular idea because the -C- material would not be vulnerable to cleavage by enzymes called glycosidases which are ubiquitous in living systems. The corollary to the increased stability of C- compared to O-glycosides is that the Lewis base/ hydrogen-bond accepting character of the natural oxygen is now replaced by a non-polar, hydrophobic CH2.

We were successful in the preparation of C-galcer, and with our principal collaborator, Dr. Moriya Tsuji (ADARC) have shown that the C-glycoside is a far superior immunostimulant than the parent O-glycoside. Recent papers from other groups throughout the world have confirmed this powerful activity. Compounds of this class of C-glycosides are now in the early stages commercial development.

Selected Publications

Identification of C-glycoside Analogues That Display A Potent Biological Activity Against Murine And Human Invariant Natural Killer T Cells. Xiangming Li, Guangwu Chen, Raquel Garcia-Navarro, Richard W. Franck and Moriya Tsuji Immunology 2009, 127, 216-225

Alpha-C-galactosylceramide as an adjuvant for a live attenuated influenza virus vaccine Kopecky-Bromberg, Sarah A.; Fraser, Kathryn A.; Pica, Natalie; Carnero, Elena; Moran,  Thomas M.; Franck, Richard W.; Tsuji, Moriya; Palese, Peter  Vaccine 2009, 27, 3766-3774

C-Galactosylceramide Diastereomers via Sharpless Asymmetric Epoxidation Chemistry. Jun Pu and Richard W. Franck Tetrahedron 2008, 64 8618-8629.

Synthesis of the Mixed Acetal Segment of S- Glyceroplasmalopsychosine. Ajit K. Parhi, David R. Mootoo and Richard W. Franck Tetrahedron 2008, 64 9821-9827.

A Single Early Activation of Invariant NK T Cells Confers Long-Term Protection against Collagen-Induced Arthritis in a Ligand-Specific Manner. Ken Coppieters, Katrien Van Beneden, Peggy Jacques, Pieter Dewint, Ann Vervloet, Bert Vander Cruyssen, Serge Van Calenbergh, Guangwu Chen, Richard W. Franck, Gust Verbruggen, Dieter Deforce, Patrick Matthys, Moriya Tsuji, Pieter Rottiers, and Dirk Elewaut J Immunol 2007, 179 2300-2309.

Combined Natural Killer T-Cell–Based Immunotherapy Eradicates Established Tumors in Mice Michele W.L. Teng, Jennifer A. Westwood, Phillip K. Darcy, Janelle Sharkey Moriya Tsuji, Richard W. Franck, Steven A. Porcelli, Gurdyal S. Besra, Kazuyoshi Takeda, Hideo Yagita, Michael H. Kershaw and Mark J. Smyth, Cancer Research 2007, 67, 7495-7504

Glycolipid alpha-C-galactosylceramide is a distinct inducer of dendritic cell function during innate and adaptive immune responses of mice, Fujii S, Shimizu K, Hemmi H, Fukui M, Bonito AJ, Chen G, Franck RW, Tsuji M, Steinman RM. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 11252-7.

E and Z alpha-C-galactosylceramides by Julia-Lythgoe- Kocienski chemistry: a test of the receptor-binding model for glycolipid immunostimulants.Chen G, Chien M, Tsuji M, Franck RW. Chembiochem. 2006, 7, 1017-22.

The Ramberg-Backlund reaction for the synthesis of C- glycosides, C-linked-disaccharides and related compounds. Taylor RJ, McAllister GD, Franck RW. Carbohydr. Res. 2006, 341, 1298-311.

Alpha-C-Galactosylceramides: Synthesis and Immunology, Richard W. Franck and Moriya Tsuji, Acct. Chem. Res. 2006, 39, 692-701.