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Iwao Ojima

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Iwao Ojima
Born (1945-06-05) June 5, 1945 (age 79)
EducationUniversity of Tokyo (B.S., M.S., Ph.D.)
AwardsACS Ernest Guenther Award (2019)

ACS Award for Creative Work in Fluorine Chemistry (2013) ACS E. B. Hershberg Award (2001) Chemical Society of Japan Award (1998)

ACS Arthur C. Cope Scholar Award (1994)
Scientific career
FieldsOrganic and Medicinal Chemistry
InstitutionsStony Brook University
Websitestonybrook.edu/commcms/ojima_group

Iwao Ojima (born June 5, 1945, in Japan) is a Japanese-American chemist and university distinguished professor at the State University of New York at Stony Brook (Stony Brook University).[1] He has been widely recognized for his seminal contributions to a range of chemical research at the multifaceted interfaces of chemical synthesis and life sciences. As rare accomplishments, he has received four National Awards from the American Chemical Society in four different fields of research. He is also serving as the director of the Institute of Chemical Biology and Drug Discovery (ICB&DD),[2] as well as the president of the Stony Brook Chapter of the National Academy of Inventors.

Biography

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Ojima was born in Yokohama, Japan, in 1945 and educated at the University of Tokyo, Japan (B.S. 1968, Ph.D. 1973).[1]  Before coming to the U.S. as an associate professor at the State University of New York at Stony Brook in 1983, he worked at the Sagami Institute of Chemical Research in Japan, first as a research fellow and later as a senior research fellow and group leader of the organometallic chemistry and organic synthesis research group.  At Stony Brook, he quickly climbed the ranks: he was promoted to professor in 1984, leading professor in 1991, and university distinguished professor in 1995. He served as department chair from 1997 to 2003 and has been serving as the founding director of the Institute of Chemical Biology and Drug Discovery (ICB&DD) since 2003,[2] as well as the president of the Stony Brook Chapter of the National Academy of Inventors from 2015.[3] He has been a visiting professor at the Université Claude Bernard Lyon I, Lyon, France (1989), the University of Tokyo, Tokyo, Japan (1996), the Scripps Research Institute, La Jolla, CA (1997), and Université de Paris XI, BIOCIS, Châtenay-Malabry, France (1997).[1] As an extracurricular activity, he has been serving as the president of the Japan Center at Stony Brook since 2004.[4]

Research areas

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In Ojima's early research career, he was mainly engaged in homogeneous catalysis of phosphine-Rh complexes, its development as new synthetic processes, as well as their applications to catalytic asymmetric synthesis and organic synthesis. He received a 25th CSJ Award for Young Investigator for his research on "Highly selective syntheses by means of organosilicon compounds – transition metal complex systems" from the Chemical Society of Japan in 1976. Through the 1970-1980s, he established himself as an authoritative scholar in catalytic asymmetric synthesis, editing a book, "Catalytic Asymmetric Synthesis" (Wiley-VCH) in 1993, and also published the second (2000) and third (2010) editions. This book collectively became a very popular reference book with >4,100 citations.[5] He was a prolific researcher in the development of new synthetic methods based on transition-metal catalyzed reactions and investigations into their mechanisms, which includes hydrosilylation, silylformylation, silylcarbocyclizations (SiCaCs, SiCaB, SiCaT), higher order (carbonylative) cycloadditions, hydroformylation, hydrocarbonylations, amidocarbonylations, cyclohydrocarbonylations, and enantioselective processes such as hydrosilylation, hydrogenation, hydroformylation, Michael addition, allylic alkylation/amination/etherification, etc.[6]

Since the late 1970s, Ojima began his work in organofluorine chemistry by exploring the interface of fluorine chemistry and organometallic chemistry/catalysis. His notable achievements include the development of processes for the highly regioselective hydroformylations of fluoro-olefins, synthesis of N-acylfluoroamino acids via hydroformylation-amidocarbonylation of fluoro-olefins, synthesis of a-trifluoromethylacrylic acid via carboxylation, novel ureidocarbonylation, synthesis of optically pure fluoroamino acids via enzymatic kinetic resolution, etc.[7]  It is noteworthy that Ojima's synthesis of trifluoromethyluracil from 2-bromotrifluoropropene became an industrial process by Japan Halon (then, Tosoh F-Tech). Furthermore, this process was successfully applied to the commercial synthesis of trifluridine (trifluorothymidine), an antiherpes antiviral drug, primarily used on the eye topically, such as "Viroptic" by Tokyo Yuki Gosei Kogyo in early 1990s.[7] His pioneering work on optically pure fluoroamino acids and their use in medicinally active compounds, such as enkephalin, captopril and taxol (paclitaxel), brought medicinal and biomedical applications to the scope of fluorine chemistry community.[7] He edited a book, "Fluorine in Medicinal Chemistry and Chemical Biology" (Wiley-Blackwell, > 1,700 citations) in 2009, featuring the basic principles and exemplary applications of fluorine incorporation to biologically relevant compounds and systems.[8]

One of his renowned achievements is the development of the "β-Lactam Synthon Method",[9][10] which has been applied to the synthesis of α- and β-amino acids, oligopeptides, peptidomimetics, taxanes and taxoids. This method has been successfully applied for the practical synthesis of the Ojima lactam, a key intermediate for the commercial production of paclitaxel (Taxol), one of the most widely used anticancer drug for chemotherapy, through the Ojima-Holton coupling,[11] as well as for the medicinal chemistry and development of new-generation taxoid anticancer agents.[11] One of his second-generation taxoids, "ortataxel", developed from 14-hydroxy-10-deacetylbaccatin III, and licensed to Indena, SpA, Italy, has advanced to the Phase II human clinical trials. The extensive SAR studies performed in his laboratory have led to the development of numerous highly potent novel second- and third-generation taxoids. The third-generation taxoids showed virtually no difference in potency against drug-resistant and drug-sensitive cell lines. Some of the next-generation taxoids also exhibited excellent potency against cancer stem cells. Other highlights include his common pharmacophore proposal for microtubule-stabilizing anticancer agents, identification of the paclitaxel binding site and its bioactive conformation in the β-tubulin based on photoaffinity labeling and computational analyses, identification of unique characteristics of the next-generation taxoids in cancer cell biology and their mechanism of action, and efficacious tumor-targeted drug delivery of highly potent next-generation taxoids.[11][12]

Currently, Ojima's research program is focused on the drug discovery and development of next-generation anticancer agents and their tumor-targeted drug delivery,[11][13] antibacterial agents,[14] antifungal agents,[15] and antinociceptive agents,[16] etc. In his research, all relevant chemistry and biological tools, including computer-aided drug design, chemical synthesis, computational biology, chemical biology and cell biology are integrated in close collaborations with structural biologists, computer biologists, cell biologists, oncologists, microbiologist, pharmacologists, anesthesiologists, toxicologists, etc.

As of January 2024, he has published >500 papers and reviews in leading journals, >100 issued patents, edited nine books, and given >135 plenary and invited lectures in international meetings. SciFinder lists >1,000 publications to his credit.

Awards and honors

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References

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  1. ^ a b c "Iwao Ojima | Chemistry". www.stonybrook.edu. Retrieved 2019-06-04.
  2. ^ a b "Stony Brook University Welcome to the Institute of Chemical Biology & Drug Discovery". www.stonybrook.edu. Retrieved 2019-06-04.
  3. ^ "Home | Chapter of the National Academy of Inventors". www.stonybrook.edu. Retrieved 2019-06-04.
  4. ^ "Home | Japan Center at Stony Brook". www.stonybrook.edu. Retrieved 2019-06-04.
  5. ^ Ojima, Iwao, ed. (2010-02-10). Catalytic Asymmetric Synthesis. Hoboken, NJ, USA: John Wiley & Sons, Inc. doi:10.1002/9780470584248. ISBN 9780470584248. S2CID 93318061.
  6. ^ "Publications list of Iwao Ojima" (PDF). Stony Brook University.
  7. ^ a b c Ojima, Iwao (2013-07-05). "Exploration of Fluorine Chemistry at the Multidisciplinary Interface of Chemistry and Biology". The Journal of Organic Chemistry. 78 (13): 6358–6383. doi:10.1021/jo400301u. ISSN 0022-3263. PMC 3752428. PMID 23614876.
  8. ^ Yamazaki, Takashi; Taguchi, Takeo; Ojima, Iwao (2009-04-03), Ojima, Iwao (ed.), "Unique Properties of Fluorine and their Relevance to Medicinal Chemistry and Chemical Biology", Fluorine in Medicinal Chemistry and Chemical Biology, John Wiley & Sons, Ltd, pp. 1–46, doi:10.1002/9781444312096.ch1, ISBN 9781444312096, S2CID 93933024
  9. ^ Ojima, Iwao (1995). "Recent Advances in the .beta.-Lactam Synthon Method". Accounts of Chemical Research. 28 (9): 383–389. doi:10.1021/ar00057a004. ISSN 0001-4842.
  10. ^ Ojima, Iwao; Delaloge, Francette (1997). "Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method". Chem. Soc. Rev. 26 (5): 377–386. doi:10.1039/CS9972600377. ISSN 0306-0012.
  11. ^ a b c d Ojima, Iwao; Wang, Xin; Jing, Yunrong; Wang, Changwei (2018-02-22). "Quest for Efficacious Next-Generation Taxoid Anticancer Agents and Their Tumor-Targeted Delivery". Journal of Natural Products. 81 (3): 703–721. doi:10.1021/acs.jnatprod.7b01012. ISSN 0163-3864. PMC 5869464. PMID 29468872.
  12. ^ Ojima, Iwao (2008). "Guided Molecular Missiles for Tumor-Targeting Chemotherapy—Case Studies Using the Second-Generation Taxoids as Warheads". Accounts of Chemical Research. 41 (1): 108–119. doi:10.1021/ar700093f. ISSN 0001-4842. PMID 17663526.
  13. ^ Ojima, Iwao (2008-04-15). "ChemInform Abstract: Guided Molecular Missiles for Tumor-Targeting Chemotherapy-Case Studies Using the Second-Generation Taxoids as Warheads". ChemInform. 39 (16). doi:10.1002/chin.200816271. ISSN 0931-7597.
  14. ^ Kumar, Kunal; Awasthi, Divya; Berger, William T; Tonge, Peter J; Slayden, Richard A; Ojima, Iwao (August 2010). "Discovery of anti-TB agents that target the cell-division protein FtsZ". Future Medicinal Chemistry. 2 (8): 1305–1323. doi:10.4155/fmc.10.220. ISSN 1756-8919. PMC 3039483. PMID 21339840.
  15. ^ Lazzarini, Cristina; Haranahalli, Krupanandan; Rieger, Robert; Ananthula, Hari Krishna; Desai, Pankaj B.; Ashbaugh, Alan; Linke, Michael J.; Cushion, Melanie T.; Ruzsicska, Bela (2018-03-05). "Acylhydrazones as Antifungal Agents Targeting the Synthesis of Fungal Sphingolipids". Antimicrobial Agents and Chemotherapy. 62 (5). doi:10.1128/aac.00156-18. ISSN 0066-4804. PMC 5923120. PMID 29507066.
  16. ^ Yan, Su; Elmes, Matthew W.; Tong, Simon; Hu, Kongzhen; Awwa, Monaf; Teng, Gary Y.H.; Jing, Yunrong; Freitag, Matthew; Gan, Qianwen (June 2018). "SAR studies on truxillic acid mono esters as a new class of antinociceptive agents targeting fatty acid binding proteins". European Journal of Medicinal Chemistry. 154: 233–252. doi:10.1016/j.ejmech.2018.04.050. ISSN 0223-5234. PMC 5999033. PMID 29803996.
  17. ^ "Arthur C. Cope Scholar Awards". American Chemical Society. Retrieved 2019-05-17.
  18. ^ "John Simon Guggenheim Foundation | Iwao Ojima". Retrieved 2019-05-22.
  19. ^ "Elected Fellows". American Association for the Advancement of Science. Retrieved 2019-05-22.
  20. ^ "CSJ Awards". www.csj.jp. Retrieved 2019-05-17.
  21. ^ "www.nyas.org".
  22. ^ "E. B. Hershberg Award for Important Discoveries in Medicinally Active Substances". American Chemical Society. Retrieved 2019-05-17.
  23. ^ "2010 ACS Fellows". American Chemical Society. Retrieved 2019-05-23.
  24. ^ "ACS 2013 National Award Winners". Chemical and Engineering News. 90 (34): 53–54. 20 August 2012.
  25. ^ "Fellows List - National Academy of Inventors". academyofinventors.org. Archived from the original on 2019-06-21. Retrieved 2019-05-23.
  26. ^ "2019 National Award Recipients". American Chemical Society. Retrieved 2019-05-06.
  27. ^ "European Academy of Sciences - Iwao Ojima". www.eurasc.org. Retrieved 2021-01-26.
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