GROUP WEB SITE
Memorial Sloan-Kettering Cancer Center, Postdoc
Columbia University, Ph.D.
Columbia University, M.Phil.
Columbia University, M.A.
Stanford University, B.A.
Edison-Lecks Chemistry Building 211
415 South Street
Waltham, MA 02454-9110
Associate Professor of Chemistry
Ph.D., Columbia University
Our lab studies interesting problems in organic synthesis and chemical biology.
Our chemical biology program is directed at the design and synthesis of carbohydrate clusters which mimic important binding surfaces in biology. One target is the portion of HIV protein gp120 which is bound by 2G12, a broadly-neutralizing antibody which protects against the virus. Good mimics of this glycocluster have potential as HIV vaccines. Rather than design and test individual glycoclusters, we are using a directed evolution-based approach, in which the best gp120 mimics are selected from a diverse glycocluster library by their ability to bind 2G12. This directed evolution is accomplished by attachment of sugars to a library of DNA sequences using click chemistry, a technique which we term SELMA (SELection with Modified Aptamers). We are also applying SELMA and related methods to other problems in molecular recognition.
Our organic synthesis program is focused on study of mechanistically-interesting reactions which enable access to structural motifs that are difficult to access by other methods. One example is homoallylation reactions. Although a great number of allylation methods are known, known methods for synthesis of the one-carbon homologs are very limited, despite their utility as precursors of stereodefined tetrahydrofurans and tetrahydropyrans. In addition to development of these methods, we are also interested in their application to synthesis of interesting target structures.
Sample of Recent Publications
Boron Carboxylate Catalysis of Homoallylboration
Dugas, G. J.; Lam, Y.-H.; Houk, K. N.; Krauss, I. J. J. Org. Chem. 2014 , ASAP (Featured Article)
- "Directed Evolution of Multivalent Glycopeptides Tightly Recognized by HIV Antibody 2G12"
Horiya, S.; Bailey, J.; Temme, J.; Guillen Schlippe, Y.; Krauss, I. J. Am. Chem. Soc., Just accepted (Highlighted in C&E News, 3/31/14)
- High Temperature SELMA: Evolution of DNA-Supported Oligomannose Clusters Which Are Tightly Recognized by HIV bnAb 2G12Temme, S. J.; MacPherson, I. S.; DeCourcey, J. F.; Krauss, I. J. J. Am. Chem. Soc. 2014 , 136(5), 1726-1729.
Confirmation of the structures of synthetic derivatives of migrastatin in the light of recently disclosed crystallographically based claimsNagorny, P.; Krauss, I. J. Njardarson, J. T.; Perez, L.; Gaul, C.; Yang, G.; Ouerfelli, O.; Danishefsky, S. J. Tetrahedron Lett. 2010, 51(30), 3873-3875.
Diverted Total Synthesis Leads to the Generation of Promising Cell-Migration Inhibitors for Treatment of Tumor Metastasis: In vivo and Mechanistic Studies on the Migrastatin Core Ether AnalogOskarsson, T.; Nagorny, P.; Krauss, I. J.; Perez, L.; Mandal, M.; Yang, G.; Ouerfelli, O.; Xiao, D.; Moore, M. S.; Massague, J.; Danishefskhy, S. J. J. Am. Chem. Soc. 2010, 132(9), 3224-3228.
A New Model for the Presentation of Tumor-Associated Antigens and the Quest for an Anticancer Vaccine: A Solution to the Synthesis Challenge via Ring-Closing MetathesisJeon, I.; Lee, D.; Krauss, I. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131(40), 14337-14344.
An oligosaccharide-based HIV-1 2G12 mimotope vaccine induces carbohydrate-specific antibodies that fail to neutralize HIV-1 virionsJoyce, J. G.; Krauss, I. J.; Song, H. C.; Opalka, D. W.; Grimm, K. M.; Nahas, D. D.; Esser, M. T.; Hrin, R.; Feng, M.; Dudkin, V. Y.; Chastain, M.; Shiver, J. W.; Danishefsky, S. J. Proc. Natl. Acad. Sci. USA 2008, 105(41), 15684-15689.
Total Synthesis of Spirotenuipesines A and BDai, M.; Krauss, I. J.; Danishefsky, S. J. J. Org. Chem. 2008, 73(24), 9576-9583.
Fully Synthetic Carbohydrate HIV Antigens Designed on the Logic of the 2G12 AntibodyKrauss, I. J.; Joyce, J. G.; Finnefrock, A. C.; Song, H. C.; Dudkin, V. Y.; Geng, X.; Warren, J. D.; Chastain, M.; Shiver, J. W.; Danishefsky, S. J. J. Am. Chem. Soc. 2007, 129(36), 11042-11044.
Total synthesis of (+)-isomigrastatinKrauss, I. J.; Mandal, M.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2007, 46(29), 5576-5579.
Highly Practical and Enantioselective Cu-Catalyzed Conjugate Addition of Alkylzinc Reagents to Cyclic Enones at Ambient TemperatureKrauss, I. J.; Leighton, J. L. Org. Lett. 2003, 5(18), 3201-3203.
Highly Regioselective and Diastereoselective Directed Hydroformylation of Allylic Ethers: A New Approach to Propionate Aldol SynthesisKrauss, I. J; Wang, C. C-Y.; Leighton, J. L. J. Am. Chem. Soc. 2000, 123(46), 11514-11515.