» Research Group web page (updated on 05.05.2008) » Open Position for Undergraduate Researchers		Yan-Yeung Luk  Assistant Professor Bioorganic chemistry; surfaces; nanomaterials; chemical biology yluk@syr.edu phone: 315-443-7440 / fax: 315-443-4070 Office: CST 3-048 Education: • B.S., 1994, Polytechnic University • Ph.D., 2001, University of Chicago • Postdoctoral Fellow, University of Wisconsin-Madison Courses: • CHE 117*: General Chemistry Laboratory • CHE 400/600*: Chemistry at the Interfaces – Biomaterials • CHE 427/627: Intermediate Organic Chemistry   * denotes current Spring '08 course

Research Interests Luk's laboratory focuses on two areas that use organic chemistry to build new bio-functional materials and novel therapeutic agents. Our research addresses both fundamental questions and application developments that will significantly impact human health. A. Functional Biocompatible Materials. This research program revolves around the development of new biocompatible materials for development of sensors and control of biointerfaces. Specifically, we are developing new bioinert surface chemistry, nanostructured gold films and protein-laden porous hydrogel materials. These studies have enabled discoveries in fundamental sciences and a broad range of applications including heterogeneous biocatalysis, control of biofouling (protein adsorption, cell adhesion and biofilm formation) on surfaces and developments of biosensors. Below are some detail elements of what we have accomplished and established so far: Development of a stable water-in-water emulsion of polymer-dispersed lyotropic liquid crystals (published in Langmuir). New porous, biocatalytic hydrogel developed from water-in-water emulsion. A biocompatible self-assembly system based on a folding surfactant (published in JACS). Control of mammalian cell adhesion by gradient nanotopography (published in JACS). Development of chemical gradients for controlling biofilm formation. Monolayer chemistry for controlling the biofilm formation (Collaboration with Dr. Ren, published in Appl. Environ. Microbiol.) Synthesized of a new class of brominated furanones that enables the study of structure-activity relationship for biofilm inhibition (soon to appear, Collaboration with Dr. Dacheng Ren). General porous coating to have a universal control of biofilm on surfaces (Collaboration with Dr. Dacheng Ren). Development of a surface gradient in bio-inert chemistry that can control the adhesion of mammalian cells. Biosensor development – novel materials established. B. Nanometric Multivalent Agents. Pharmaceutical industry usually avoids the weak biological binding as targets for drug discovery and development. In this research program, we develop expeditious synthetic routes and methodologies for small molecules that inhibit mammalian cell adhesion, and incorporate these molecules into nanometric multivalent agents to function as therapeutic molecules that utilize the weak bindings in biological systems. Specifically, we develop novel trivalent molecules with controlled sizes that selectively bind targeted membrane protein integrin on mammalian cell surfaces. These integrin antagonists have therapeutic potential for multiple diseases. Below are some detail elements of what we have accomplished and established so far: Development of a water-driven chemoselective reaction between squarate derivative and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. (published in Org. Lett.) Utilized the developed chemoselective reaction to couple two unprotected peptides together and to synthesize a general water stable labeling reagent to label proteins and cell surfaces. Development of efficient synthesis of new drugs (integrin antagonists) that has a potency of IC50 < 10 nM for inhibiting cell adhesion. The synthesis consists of 1 to 4 steps; one specific example arrives at the product by a one-spot synthesis without protecting groups in water. Regio-specific synthesis of C3-dissymmetric keystone molecules. Synthesis and resolution of C3-dissymmetric chimera molecules of synthetic core tethered with amino acids – will tether integrin antagonists soon. Chiral Molecules with T, O and I Symmetry: Theoretical Solutions to a Difficult Problem in Stereochemistry. Selected Publications Utilizing the high dielectric constant of water: efficient synthesis of amino acid-derivatized cyclobutenones Jun Li, Yongbin Han, Teresa B. Freedman, Shifa Zhu, Deborah J. Kerwood and Yan-Yeung Luk*, Tet. Lett., 2008, 49(13), 2128-2131. » full article Chiral Molecules with Polyhedral T, O or I Symmetry: Theoretical Solution to A Difficult Problem in Stereochemistry Sri Kamesh Narasimhan, Xiaoying Lu and Yan-Yeung Luk* Chirality In press. 2008. » full article Identifying the important structural elements of brominated furanones for inhibiting biofilm formation by Escherichia coli Yongbin Han, Shuyu Hou, Karen A. Simon, Dacheng Ren* and Yan-Yeung Luk*, Bioorg. Med. Chem. Lett., 2008, 18(3), 1006-1010. » full article Water-Driven Chemoselective Reaction of Squarate Derivatives with Amino Acids and Peptides Preeti Sejwal, Yongbin Han, Akshay Shah and Yan-Yeung Luk*, Org. Lett., 2007, 9, 4897-4900. » full article Enhancing Cell Adhesion and Confinement by Gradient Nanotopography Karen A. Simon, Erik A. Burton, Yongbin Han, Jun Li, Anny Huang and Yan-Yeung Luk*, J. Am. Chem. Soc., 2007, 129, 4892-4893. » full article Water-in-Water Emulsions Stabilized by Non-Amphiphilic Interactions: Polymer-Dispersed Lyotropic Liquid Crystals Karen A. Simon, Preeti Sejwal, Ryan B. Gerecht, Yan-Yeung Luk*, Langmuir, 2007, 23, 1453-8. » full article A Biocompatible Surfactant with Folded Hydrophilic Head Group: Enhancing the Stability of Self-Inclusion Complexes of Ferrocenyl in a β-Cyclodextrin Unit by Bond Rigidity Yongbin Han, Kejun Cheng, Karen A. Simon, Yanmei Lan, Preeti Sejwal, Yan-Yeung Luk*, J. Am. Chem. Soc., 2006, 128, 13913-20. » full article Inhibiting Escherichia Coli Biofilm Formation by Self-Assembled Monolayers of Functional Alkanethiols on Gold Shuyu Hou, Erik A. Burton, Karen A. Simon, Dustin Blodgett, Yan-Yeung Luk* and Dacheng Ren*, Appl. Environ. Microbiol. 2007, 73, 4300-4307. » full article Surface-Driven Switching of Liquid Crystals using Redox-Active Groups on Electrodes Yan-Yeung Luk, Nicholas L. Abbott,* Science, 2003, 301, 623-6. » View all Publications