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Mark A. Lipton
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Devlopment of Novel Synthetic Methodology

Projects in this area stem from our own needs for new organic transformations or, more generally, from a recognized need in the organic chemistry community for a new method. In the former vein, we have developed new reagents for the guanylation of amines (i.e., their conversion to guanidines) [link, link] and the protection of carboxylic acids as dimethylallyl (DMA) esters [link], link] In the latter vein, we developed a novel, cyclic dipeptide catalyst for an asymmetric version of the Strecker amino acid synthesis [link, link]. This latter finding led to a broad effort directed toward the use of cyclic dipeptide catalysts in asymmetric carbon-carbon bond forming reactions [link, link]. This work has been highlighted in Chemical and Engineering News (April 28, 1997; p. 26-27; May 19, 1997; p. 38-40).  Current projects involve the synthesis of macrocyclic lactams and thioesters on a solid support as well as new methods for forming amide bonds.

Hncb

Design and Synthesis of Biologically Active Molecules

Research in this area can be thought of as "drug design." We have earlier studied the cytotoxicity of the marine depsipeptide callipletin B [link].  We have also made pseudopeptide inhibitors of the HIV-1 protease [link, link].  We have also studied the origin of the so-called “French Paradox” by making a library of analogues of the phytoalexin resveratrol and testing its ability to inhibit a number of biological targets [link, link].  Ongoing projects include the synthesis of inhibitors of the enzymes HMG CoA Reductase – a novel target for antimicrobial design --and Ghrelin O-Acyl Transferase the synthesis of novel DNA-cleaving agents for the treatment of cancers, especially those leading to solid tumor formation. Projects of this type usually involved computer-aided molecular modeling, X-ray crystallography and enzyme inhibition studies.

HMGR scheme
HMGRcs

Updated August 2017