Isaac Krauss

Isaac KraussAssociate Professor of Chemistry

Group Lab Site

Curriculum Vitae (PDF)

Degrees

Columbia University, PhD
Columbia University, MPhil
Columbia University, MA
Stanford University, BA

Profile

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.

GlycoDNAs

The SELMA Method

Bromophycolide AOur 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.

Homoallylation

Selected Publications

"Antibody recognition of HIV and dengue glycoproteins." Krauss IJ. Glycobiology. 2016 Mar 3. pii: cww031

"SELMA: Selection with Modified Aptamers." Temme, J. S.; Krauss I. J. Curr. Protoc. Chem. Biol. 2015 , 7, 73-92.

"Recent Strategies Targeting HIV Glycans in Vaccine Design." Horiya, S.; MacPherson, I. S.; Krauss I. J. Nat. Chem. Biol. 2014 ,10, 990-999.

"Enantioselective syn and anti Homocrotylation of Aldehydes: Application to the Formal Synthesis of Spongidepsin." Lin, H. K.; Tian, L.; Krauss, I. J. J. Am. Chem. Soc. 2015 Oct 14;137(40):13176-82.

"Recent Strategies Targeting HIV Glycans in Vaccine Design." Horiya, S.; MacPherson, I. S.; Krauss I. J. Nat. Chem. Biol. 2014 ,10, 990-999.

"Boron Carboxylate Catalysis of Homoallylboration." Dugas, G. J.; Lam, Y.-H.; Houk, K. N.; Krauss, I. J. J. Org. Chem. 2014 ,79(10), 4277-4284. (Featured Article)

"Directed Evolution of Multivalent Glycopeptides Tightly Recognized by HIV Antibody 2G12." Horiya, S.; Bailey, J. K.; Temme, S. J.; Guillen-Schlippe, Y. V.; Krauss, I. J. J. Am. Chem. Soc. 2014, 136(14), 5407-5415 . (Highlighted in C&E News, 3/31/2014) Access the recommendation on F1000Prime

"High Temperature SELMA: Evolution of DNA-Supported Oligomannose Clusters Which Are Tightly Recognized by HIV bnAb 2G12." Temme, S. J.; MacPherson, I. S.; DeCourcey, J. F.; Krauss, I. J. J. Am. Chem. Soc. 2014, 136(5), 1726-1729. Access the recommendation on F1000Prime

"Homoallylboration and Homocrotylboration of Aldehydes." Pei, W.; Krauss, I. J. J. Am. Chem. Soc. 2011, 133(46), 18514-18517. (Highlighted in Synfacts 2012, 8, 203).

"Multivalent Glycocluster Design Through Directed Evolution." MacPherson, I. S.; Temme. J. S.; Habeshian, S.; Felczak, K.; Pankiewicz, K.; Hedstrom, L.; Krauss, I. J.  Angew. Chem. Int. Ed. 2011, 50(47), 11238-11242.

For a complete list of publications, see the complete Curriculum Vitae (PDF).