Mark A. LiptonAssociate Professor—Organic Chemistry/Chemical Biology
Office: WTHR 409
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Our research effort combines the disciplines of organic synthesis, bioorganic chemistry and molecular modeling. Current projects in the Lipton group fall into two areas:
Development of novel synthetic methodology.
We have recently developed two new reagents for the guanylation of amines, an important and underdeveloped reaction. We also have developed a novel, cyclic dipeptide catalyst (1) for an asymmetric variant of the Strecker amino acid synthesis. This has led to a broad effort directed toward the use of cyclic dipeptide catalysts (e.g., 2) in asymmetric carbon-carbon bond forming reactions. We have initiated another broad effort in the area of reactions on solid supports. We began with the synthesis of cyclic dipeptides 1 and 2 for our catalysis studies. Recent projects involve the synthesis of peptidomimetics (e.g., 3) and macrocyclic lactams on solid supports.
Design and synthesis of biologically active molecules.
Ongoing projects include the synthesis of inhibitors of the enzymes cyclophilin A and HIV-1 protease (both essential for the replication of the HIV-1 virus and the pathogenesis of AIDS), and novel DNA-cleaving agents for the treatment of cancer. Projects of this type usually are designed using molecular modeling and tested "in house" after synthesis.
EducationB.S., 1981, Harvey Mudd College; M.A., 1984, M.Ph., 1986, Ph.D., 1988, Columbia University; Postdoctoral Fellow, 1988-1990, University of California, Berkeley.
- Bekele T.;Christian, C. F.;Lipton, M. A.;Singleton, D. A., "Concerted" transition state, stepwise mechanism. dynamics effects in (C2-C6) enyne allene cyclizations. Journal of the American Chemical Society 2005 , 127 , 9216-9223.
- Kang S. S.;Cuendet, M.;Endringer, D. C.;Croy, V. L.;Pezzuto, J. M.;Lipton, M. A., Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappa B . Bioorganic & Medicinal Chemistry 2009 , 17 , 1044-1054.
- Ramamoorthy G.;Acevedo, C. M.;Alvira, E.;Lipton, M. A., Synthesis and spectroscopic correlation of the diastereoisomers of 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid: implications for the structures of papuamides A-D and mirabamides A-D . Tetrahedron-Asymmetry 2008 , 19 , 2546-2554.
- Krishnamoorthy R.;Richardson, B. L.;Lipton, M. A., Synthesis and cytotoxicity of desmethoxycallipeltin B: Lack of a quinone methide for the cytotoxicity of callipeltin B . Bioorganic & Medicinal Chemistry Letters 2007 , 17 , 5136-5138.