É«ÖÐÉ«

• Ph.D., Organic Chemistry (UCLA): 1986
• NIH Post-doctoral Fellow, Synthetic Organic Chemistry (MIT): 1987

One area of interest in our research group is the synthesis of a wide structural range of organophosphorus compounds that can potentially act as selective inhibitors of acetylcholinesterase and butyrylcholinesterase, a family of enzymes that hydrolyzes acetylcholine. In Alzheimer patients, butyrylcholinesterase is over-expressed and thus is primarily responsible for acetylcholine hydrolysis that results in the loss of cognitive function. Thus, the development of inhibitors selective for butyrylcholinesterase may result in drugs that are effective in the treatment of the progression of this disease.

Our group is also active in the development of new synthetic methods. Recently, we established that tin(II) salts can catalyze the three-component reaction between an amine, aldehyde, and a phosphite to produce alpha-aminophosphonates in mild, solvent-free conditions. We are currently investigating asymmetric versions of this methodology.

M.S. Students

• Jon D. Rainier: 1987-1990 (UC Riverside, Ph.D. program in chemistry, currently chemistry faculty at the University of Utah)
• Hossein Razavi: 1991-1994 (U. of Arizona, Ph.D. program in chemistry)
• Patrick Middleton: 1993-1995 (Fountain Valley School District)
• Sotiria Contos: 2001-2004 (UCLA, Ph.D. program in chemistry)
• Eunice Cheung: 2006-2009 (Director, Learning Garden Teaching Center, Torrance, CA)
• Ricardo Gallardo-Macias: 2007-2009 (Yale University, Ph.D. program in chemistry)
• Astor Suriano: 2007-2013 (Johnson and Johnson)
• Kim Ngan Tu: 2009-2012 (UCI, Ph.D. program in chemistry)
• Trina Tran: 2011-present
• Jackson Zhu: 2012-present

B.S./B.A. Students

From 2005 onward:

• Cameron Smith: 2003-2005 (UC Berkeley, Ph.D. program in chemistry)
• Jennifer Casey: 2005-2006 (UC Berkeley; Ph.D. program in chemistry)
• Elizabeth Jaggers: 2005-2006
• Connie Cajavilca: 2005-2007 (UCI School of Medicine)
• Aimee Deconinck: 2005-2006 (science education, É«ÖÐÉ«)
• Christopher Bruner: 2007-2008 (Stanford University, PhD. program in chemistry)
• Joel Ancheta: 2007-2008 (É«ÖÐÉ«, M.S. program in physical therapy)
• Junghye Lee: 2008-2009
• Juan Gurrero: 2009-2010
• Carmen Castillo: 2009-2010 (CSUDH, accelerated secondary teacher credential program)
• Omar Gallegos: 2010-2011 (Bocchi Labs, Santa Clarita, CA)
• Elise Van Fossen: 2010-2011: (É«ÖÐÉ« MS program in biochemistry)
• Trina Tran: 2011 (É«ÖÐÉ«, MS program in chemistry)
• Robert Esquivel: 2011-2012
• Nick Spurlock: 2011-2012
• Silvia Cervantes: 2012-2013 (USC, MS program in biochemistry)
• Tina (Dung N.) Vo: 2011-2012 (Precision Aerospace Corporation)
• Phoung Anh Nguyen: 2013-present
• Minh Nguyen: 2013-present

• Kensaku Nakayama and Wayne J. Thompson, "A Highly Enantioselective Synthesis of Phosphate Triesters", J. Amer. Chem. Soc. 1990,112 , 6936-6942.
• Ken-Shing Law, Roger A. Acey, Cameron R. Smith, David A. Benton, Shelia Soroshian, Brett Eckenrod, Rachel Stedman, Katherine A. Kantardjieff, Kensaku Nakayama, "Dialkyl Phenyl Phosphates as Novel Selective Inhibitors of Butyrylcholinesterase", Biochemical and Biophysical Research Communications 2007, 355 , 371-378.
• Roger A. Acey and Kensaku Nakayama, Butyrylcholinesterase Inhibitors. Patent Pending (10/31/07). Application Number PCT/US2007/083262 Ramses B. Toma, Gail C. Frank, Kensaku Nakayama and Eman Tawfik, "Lycopene Content in Raw Tomato Varieties and Tomato products", J. of Foodservice 2008, 19, 127-132.
• Ricardo Gallardo-Macias and Kensaku Nakayama, "Sn(II) Compounds as Catalysts for the Kabachnik-Fields Reaction Under Solvent Free Conditions: Facile Synthesis of alpha-Aminophosphonates", Synthesis 2010, 57-62.
• Thomas Casey, Kensaku Nakayama and Louis Zweier, "Sharing Innovations in STEM Education Through Digital Stories: A Case Study in Organic Chemistry", Chem. Educator 2012, 17, 1-8.

• Junghye Lee* and Kensaku Nakayama, "Preliminary Studies in the Enantioselective Synthesis of Alpha-Aminophosphonates", 2008 Student Research Symposium, É«ÖÐÉ«, Sept. 12, 2008. Poster #29.
• Junghye Lee* and Kensaku Nakayama, "Preliminary Studies in the Enantioselective Synthesis of Alpha-Aminophosphonates", 2008 Southern California Conference on Undergraduate Research, Cal Poly Pomona, Nov. 22, 2008. Poster-150.
• Ricardo Gallardo-Macias* and Kensaku Nakayama, "Synthesis of Alpha-Aminophosphonates Under Solvent Free, Environmentally Friendly Conditions", É«ÖÐÉ« Research Competition, February 27, 2009. Awarded first place in the area of physical sciences and mathematics.
• Junghye Lee* and Kensaku Nakayama, "Studies in the Stereoselective Synthesis of Alpha-Aminophosphonates from Chiral Cyclic Phosphites", Southern California Undergraduate Research Conference in Chemistry and Biochemistry, USC, April 25, 2009.
• Ricardo Gallardo-Macias* and Kensaku Nakayama, "Synthesis of Alpha-Aminophosphonates Under Solvent Free, Environmentally Friendly Conditions", 23rd CSU System-wide Student Research Competition, CSULA, May 2, 2009. Session #18. Awarded 1st place in the area of physical and mathematical sciences.
• Michael W. Brown, Felisha M. Cage, Kensaku Nakayama, and Roger A. Acey, .Organic Phosphate/Phosphonate Inhibitors of Butyrylcholinesterase: Potential Therapeutics for Alzheimer.s Disease,. É«ÖÐÉ« Research Symposium, September 18, 2009.
• Felisha M. Cage, Joselyn S. Del Cid, Michael W. Brown, Kensaku Nakayama, and Roger A. Acey, .Organic Phosphate Inhibitors of Butyrylcholinesterase: Potential Therapeutics for Alzheimer.s Disease,. CSUPERB 22nd Annual Biotechnology Symposium, Santa Clara, CA. January 9, 2010.
• Elise Van Fossen*, Omar Gallegos, Carmen Castillo, and Kensaku Nakayama .Synthesis of Novel Single and Homobivalent Phosphate Compounds as Cholinesterase Inhibitors,. 2010 Student Research Symposium, É«ÖÐÉ«, Sept. 10, 2010. Poster #43.
• Kensaku Nakayama, .Organophosphorus Compounds as Highly Selective Butyrylcholinesterase Inhibitors: Synthesis and Enzyme Inhibition Studies,. 2011 CNSM Faculty Research Symposium, É«ÖÐÉ«, March 4, 2011.
• Acey, R.A.; Del Cid, J.S.; Cage, F.M.; Poynter, S.T.; MacArthur, C.; Nakayama, K. .Dialkyl Aryl Phosphate Inhibitors of Butyrylcholinesterase as a Potential Therapeutic for the Treatment of Alzheimer.s Disease: Characteristics of Off-target Effects,. ASBMB Meeting, April 9 . 13, 2011, Washington, D.C. Abs. 763.1.
• Del Cid, J.S.; Poynter, S.T.; Nakayama, K.; Acey, R.A. .Dialkyl Aryl Phosphate Inhibitors of Butyrylcholinesterase as a Potential Therapeutic for the Treatment of Alzheimer.s Disease: Characteristics of Off-target Effects., Council of Undergraduate Research, .Poster on the Hill., April 12-13, 2011, Washington, D.C. Abs. E1.
• Elise Van Fossen*, Omar Gallegos, Robert Esquivel, Nick Spurlock, Trina Tran, Reyna Raya, Roger A. Acey, and Kensaku Nakayama, "Synthesis of Novel Single and Homobivalent Phosphate.s as Cholinesterase Inhibitors", Southern California Undergraduate Research Conference in Chemistry and Biochemistry, UCSB, April 23, 2011.
• Kim Ngan Tu, Nick Spurlock, Robert Esquivel, Roger Acey, and Kensaku Nakayama, .Tetraalkyl Bis-phosphates as Bivalent Inhibitors of Butyrylcholinesterase: Compounds with Potential for the Treatment of Alzheimer.s Disease., 43nd Western Regional ACS Meeting, Pasadena Westin Hotel, Pasadena, CA. Nov. 10, 2011. Poster No.RM WRM 18.
• Turner, A.D.; Thou, C.; Nakayama, K.; Acey, R.A. .Effects of Aryl Dialkyl Phosphates on Butyrylcholinesterase., Annual Biomedical Research Conference for Minority Students, St. Louis, MO. Nov. 10-12, 2011.
• Kim NganTu, Nick Spurlock, Robert Esquivel, Roger Acey, and Kensaku Nakayama, .TetraalkylBis-phosphates as Bivalent Inhibitors of Butyrylcholinesterase-Compounds with potential for the Treatment of Alzheimer.s Disease., 22nd Annual Long Beach Research Symposium, VA Long Beach Healthcare System, Pantages Theater, Long Beach, CA. Nov. 18, 2011.
• Tu, K.N.; Suriano, A.; Tran, T.; Van Fossen, E.; Spurlock, N.; Gallegos, O.; Esquivel, R.; Feng, J.J.; Turner, A.D.; Nakayama, K.; Acey, R.A. Tetraalkyl Bisphosphates as Bivalent Inhibitors of Butyrlcholinesterase: Compounds with Potential for treatment of Alzheimer.s Disease., ACS National Meeting, Division of Medicinal Chemistry, Abst. 113. March 25, 2012, San Diego, CA.
• Feng, J.J.; Turner, A.D.; Tu, K.N.; Nakayama, K.; Acey, R.A. .Effects of Tetra-Alkyl Bis Phosphates on Butyrylcholinesterase., American Society for Biochemistry and Molecular Biology Meeting, April 20-25, 2012, San Diego, CA. Abs. LB242.
• Hartman, L.K.; Del Cid, J.S.; Nakayama, K.; Acey, R.A. .Di-n-Butyl 2-Chlorophenylphosphate as a Potential Therapeutic for Alzheimer.s Disease., American Society for Biochemistry and Molecular Biology Meeting, April 20-25, 2012, San Diego, CA. Abs. LB238.
• Vo, D. N. P.; Cervantes, S. A.; Tu, K. N.; Suriano, A.; Tran, T.; Feng, J. J.; Lara, G. P.; Turner, A. D.; Acey, R.; Nakayama, K. . Bis-Phosphates as Inhibitors of Butyrylcholinesterase: Compounds with Potential for the Treatment of Alzheimer.s Disease,. August 1, 2012, UCI Undergraduate Chemistry Symposium.
• Turner, A. D.; Acey, R. A.; Feng, J. J.; Tu, K. N.; Nakayama, K. .Effects of Tetra-alkyl Bis-phosphates on Cholinesterases,. 2012 Annual Biomedical Research Conference for Minority Students (ABRCMS).Nov. 9, 2012, San Jose, CA. Poster #D205.
• Nakayama, K. .Promoting Student Engagement in Large Classes,. Lunch and Learn Panelist, Nov. 16, 2012. CNSM, É«ÖÐÉ«.
• Tu, K.; Vo, D. N. P.; Acey, R.; Nakayama, K. .Tetra-Alkyl Bis-Phosphates as Bivalent Inhibitors of Butyrylcholinesterase: Compounds with Potential for the Treatment of Alzheimer.s Disease,. 25th Annual CSU Biotechnology Symposium, January 4, 2013, Anaheim, CA. Poster #32.
• Nakayama, K. .Organic Phosphates as Inhibitor of Butyrylcholinesterase . A Potential Treatment for Alzheimer.s Disease,. Speaker for the Bridges to the Baccalaureate Faculty Luncheon, January 11, 1013, Cerritos College, Cerritos, CA.
• Nakayama, K. .Organic Phosphates as Inhibitor of Butyrylcholinesterase . A Potential Treatment for Alzheimer.s Disease,. Speaker for the Bridges to the Baccalaureate Speaker, February 13, 1013, Cerritos College, Cerritos, CA.
• Nakayama, K. .Organic Phosphates as Inhibitor of Butyrylcholinesterase . A Potential Treatment for Alzheimer.s Disease,. Speaker for the Bridges to the Baccalaureate Speaker, February 20, 1013, Long Beach City College, Long Beach, CA.
• Nakayama, K. .Our Recent Work with Organophosphorus Compounds: Potential Butyrylcholinesterase Inhibitors,. Seminar Speaker, Sept. 25, 2013, Fullerton College, Fullerton, CA.