Norito Takenaka

Associate Professor | Biomedical and Chemical Engineering and Sciences

Contact Information

ntakenaka@fit.edu
(321) 674-7310
F.W. Olin Physical Sciences, 220

Educational Background

B.A./M.A., Boston University, 1996

Ph.D., The University of Chicago, 2002

Professional Experience

Associate Professor, Florida Institute of Technology, 2015 —

Visiting Associate Professor, Florida Institute of Technology, 2014-2015

Assistant Professor, University of Miami, 2005-2014

Postdoctoral Fellow, University of Chicago, 2002-2005

Additional Duties

In addition to teaching courses and conducting researches, I supervise the organic chemistry graduate teaching assistants and work with the chemistry stockroom staff to ensure that students learn as much as possible in the laboratory class.

Current Courses

I teach organic chemistry courses (CHM2001 & 2002) and a spectroscopy course (CHM5501).

Selected Publications

Independent Publications

17) Narcis, M. J.; Takenaka, N. “Helical-Chiral Small Molecules in Asymmetric Catalysis” Eur. J. Org. Chem.2014, 21-34. (This work was among the 25 most accessed articles of the year.)

16) Peng, Z.; Narcis, M. J.; Takenaka, N. “Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts” Molecules201318, 9982-9998.

15) Peng, Z.; Takenaka, N. “Application of Helical-Chiral Pyridines as Organocatalysts in Asymmetric Synthesis” The Chemical Record201313, 28- 42.

14) Narcis, M. J.; Sprague, D. J.; Captain, B.; Takenaka, N. “Enantio- and periselective nitroalkene Diels-Alder reaction” Org. Biomol. Chem.201210, 9134-9136.

13) Chen, J.; Captain, B.; Takenaka, N. “Helical Chiral 2,2’-Bipyridine N-Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane” Org. Lett.201113, 1654-1657.

12) Aguado, A.; Takenaka, N. “Intramolecular Nitroalkene Diels-Alder Reaction Catalyzed by Brønsted Acids” Synlett20119, 1259-1261.

11) Takenaka, N.; Chen, J.; Captain, B.; Sarangthem, R. S.; Chandrakumar, A. “Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts” J. Am. Chem. Soc. 2010132, 4536-4537. (Highlighted in Synfact 20106, 712.)

10) Chen, J.; Takenaka, N. “Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts” Chem. Eur. J. 200915, 7268-7276.

9) Takenaka, N.; Sarangthem, R. S.; Captain, B. “Helical-Chiral Pyridine N-Oxides, a New Family of Asymmetric Catalysts” Angew. Chem. Int. Ed. 200847, 9708- 9710. (This work was among the 12 most accessed articles of the month.)

8) Takenaka, N.; Sarangthem, R. S.; Seerla, S. K. “2-Aminopyridinium Ions Activate Nitroalkenes through Hydrogen Bonding” Org. Lett.20079, 2819- 2822.

Undergraduate, Graduate and Postdoctoral Publications

7) Takenaka, N.; Abel, J. P.; Yamamoto, H. “Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-Quinolinolato) Aluminum Complexes” J. Am. Chem. Soc. 2007129, 742-743.

6) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. “Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels-Alder Reactions through Hydrogen Bonding” J. Am. Chem. Soc. 2005127, 1336-1337.

5) Takenaka, N.; Xia, G.; Yamamoto, H. “Catalytic, Highly Enantio- and Diastereoselective Pinacol Coupling Reaction with a New Tethered Bis(8- quinolinolato) Ligand” J. Am. Chem. Soc. 2004126, 13198-13199.

4) Takenaka, N.; Huang, Y.; Rawal, V. H. “The First Catalytic Enantioselective Diels-Alder Reactions of 1,2-Dihydropyridine: Efficient Syntheses of Optically Active 2-Azabicyclo-[2.2.2]octanes with Chiral BINAM Derived Cr (III) Salen Complexes” Tetrahedron200258, 8299-8305.

3) Hu, T.; Takenaka, N.; Panek, J. S. “Asymmetric Crotylation Reactions in the Synthesis of Polypropionate Derived Macrolide: Application to the Total Synthesis of Oleandolide” J. Am. Chem. Soc. 2002124, 12806-12815.

2) Hu, T.; Takenaka, N.; Panek, J. S. “Total Synthesis of Oleandolide” J. Am. Chem. Soc. 1999121, 9229-9230.

1) Jain, N. F.; Takenaka, N.; Panek, J. S. “Double-Stereodifferentiating Crotylation Reactions with Chiral (E)-Crotylsilanes. Evaluation of a New Approach for the Synthesis of Polypropionate-Derived Natural Products” J. Am. Chem. Soc. 1996118, 12475-12476.

Recognition & Awards

AWARDS and HONORS

2008, Thieme Chemistry Journals Award (Germany)

2007, University of Miami Provost Award

2006, Summer Award in the Natural Sciences and Engineering, University of Miami

2006, University of Miami Provost Award

 

GRANTS and CONTRACTS

2012-2016, National Science Foundation, Chemical Synthesis Program

2007-2010, James and Esther King Biomedical Research Program

2007-2008, American Cancer Society IRG

Research

Development of New Artificial Enzymes

Drug therapy is among the most successful and reliable treatments for various health issues. However, it is impeded by limitations in chemists’ ability to make the absolutely “correct” drug molecule in a timely and cost-effective manner. The development of artificial enzymes is a new approach in chemistry dedicated to the preparation of molecules with defined 3-D structure (molecular shape), and is of paramount importance to the drug discovery and development because the function of a drug is determined by its overall shape.

Researchers in the Takenaka Lab have developed a new class of artificial enzymes that shape-selectively synthesize molecules with the desired 3-D structure from easily available chemicals. Such technology will provide scientists ready access to precious medicinally active agents, and thus will not only accelerate the drug discovery process, but also lower costs of prescription drugs.

Synthesis of Natural Products

Natural products are the secondary metabolites (small organic molecules) produced in organisms and have long been the source of the great majority of drugs and drug candidates. Indeed, 78% of the antibacterial compounds and 74% of anticancer agents available today are either natural products or their chemical derivatives. The complete chemical synthesis of natural products is the first and key step in such drug discovery endeavors that aim to treat currently incurable diseases.

The researchers in the Takenaka Lab are currently working toward the complete chemical synthesis of the alkaloid Acutumine isolated from the moonseed Sinomenium acutum.

Research & Project Interests

The Takenaka group is interested in synthetic organic chemistry in broad terms, which range from asymmetric catalysis to synthesis of complex natural products. New methods offer new ways to assemble the complex molecular architecture and execution of resulting new synthetic strategies, in turn, lead to new insights and discoveries in method development. Methodology and synthesis are expected to complement to each other. The group’s focus is on the design and development of conceptually new catalysts for the promotion of selective chemical transformations of broad synthetic utility. Of particular interest is the development of environmentally benign, highly versatile Lewis/Brønsted acids that catalyze carbon-carbon bond formation with the highest level of selectivity and efficiency, which is of central importance in organic synthesis. The second major focus of our program is on the synthesis of structurally interesting and biologically significant natural products that not only encompass our own synthetic methods but also inspire further methodology and strategy development, including mechanistic aspects. The objectives of such endeavors are the discovery and development of new synthetic technology that provides efficient access to potential pharmaceuticals in green, non-toxic fashion, as well as better understanding of organic chemistry.