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Development of New Reactions, Reagents/Catalysts, and Biologically Active Compounds
As the laboratory name means, "molecular design" is important in order to create new reactions and functional molecules such as pharmaceuticals. Our laboratory aims to develop new reactions, reagents/catalysts, and biologically active compounds, and to elucidate their mechanisms using computational chemistry in addition to trial-and-error experiments.
News & Topics
2024/12/20
New laboratory members (seven 3rd grade students) have joined our group!
2024/11/24
Mr. Mustapha Kobina Abeka gave an oral presentation at the 41st Annual Meeting of the Pharmaceutical Society of Japan, Kyushu-Yamaguchi Brach at Sojo University (C-25).
2024/06/01
Mr. Yuki Hashimoto has joined our group as Assistant!
2024/04/01
Assistant Professor Yuhei Ohta has been appointed as Assistant Professor at Graduate School of Pharmaceutical Sciences, Nagoya City University. Good luck in the new position!
2024/03/29
Mr. Mustapha Kobina Abeka gave a poster presentation at the 144th Annual Meeting of the Pharmaceutical Society of Japan in Yokohama (29P-pm044S).
2024/03/20
Seven 6th grade students from our laboratory have graduated. Congratulations!
2024/02/05
Two alumni of our laboratory visited us.
We held a welcome party for 3rd year students.
2023/12/15
Seven 3rd year students have joined our laboratory.
2023/12/04
We have launched a website.
2023/11/01
Dr. Alex Boateng became a postdoctoral fellow at Peptide Research Center, Chubu University (Prof. Hisashi Yamamoto Laboratory). Good luck in the new position!
2023/10/02
Mr. Mustapha Kobina Abeka, an international student from Ghana, has joined us as a doctoral student.
2023/09/29
Mr. Alex Boateng received the Ph.D. degree (Pharmacy).
We held Congratulations Party (Alex's PhD, 6th year students' graduation research presentation, 5th year students' clinical pharmacy practice) & Welcome Party (Mustapha).
2023/04/01
Associate Professor Koki Yamaguchi has been promoted to Professor in Laboratory of Analytical Chemistry.
Assistant Professor Yuhei Ohta has joined our laboratory as Assistant Professor from Laboratory of Analytical Chemistry.
2019/11/16
Mr. Takuto Yoshimitsu received the Excellent Presentation Award at the 36th Kyushu Branch Conference of the Pharmaceutical Society of Japan (Nagasaki University).
2019/10/01
Mr. Alex Boateng, an international student from Ghana, has joined us as a doctoral student.
2018/04/01
Professor Masaharu Sugiura has been appointed.
Group Members
STUFFS
Professor
Masaharu Sugiura (e-mail: msugiura(at)ph.sojo-u.ac.jp)
Assistant
Yuki Hashimoto (e-mail: hashi05(at)ph.sojo-u.ac.jp)
STUDENTS
2nd grade Doctoral Course
Mustapha Kobina ABEKA
6th grade Undergraduate
Mizuki Kawabata, Shoko Dantani, Moyu Teshima, Kotomi Tominaga, Mio Yamaguchi, Mei Yamaguchi, Wakana Yokota
5th grade Undergraduate
Shota Izumi, Akito Konya, Yuki Sasaki, Mao Nonoguchi, Haruna Hamasaki, Kanan Matsumori, Ranka Murayama
4th grade Undergraduate
Taichi Ayabe, Mitsuki Imamura, Ai Kadekawa, Miyu Kawase, Suzuna Tachibana, Sumire Hayashida, Ayu Maehata
3rd grade Undergraduate
Rise Awata, Ayaka Kajihara, Neo Kawakami, Anji Koga, Hazuki Sakanoue, Kana Yamaguchi, Moeka Morishita
Research
1. Development of One-pot Synthetic Method for α,β-Unsaturated Carbonyl Compounds
We have developed an aldol condensation reaction (one-pot synthetic method for α,β-unsaturated carbonyl compounds) using titanium tetrachloride as a condensing agent (see the figure below, ref. 1). This method enables aldol condensations that could not be performed under classical conditions.
For example, the reaction between two simple ketones allows one-pot synthesis of various β,β-disubstituted α,β-unsaturated ketones (ref. 2). ar-Atlantone and its analogues synthesized using this method were found to have neuroprotective effect on dopamine neurons (ref. 3, collaboration with Prof. Takahiro Seki, Himeji Dokkyo University).
The reaction between thioesters and various conjugated unsaturated aldehydes provides polyenyl thioesters, which can be used as synthetic intermediates for the synthesis of polyene natural products (ref. 4).
Various unsaturated selenoesters can be also synthesized by the reaction between selenoesters and aldehydes. The prepared unsaturated selenoesters were found to have multiple antiviral activities against HIV-1, SARS-CoV-2, and Hepatitis B Virus (ref. 5, collaboration with Prof. Masayuki Amano, Kumamoto University).
References: (1) J. Synth. Org. Chem., Jpn. 2024, 82, 570–580. (2) J. Org. Chem. 2015, 80, 8830–8835. (3) Cells 2021, 10, 1090. (4) Tetrahedron Lett. 2020, 61, 152280. (5) ACS Omega 2023, 8, 1369–1374.
2. Activation of Trichlorosilane by Lewis Base Catalyst
We have developed a variety of new reactions based on activation of trichlorosilane by Lewis base catalysts (see the figure below). For example, β,β-disubstituted α,β-unsaturated ketone, synthesized by the one-pot synthetic method described above, undergo asymmetric conjugate reduction to give a variety of β-chiral ketones with high enantioselectivity (ref. 1, 2). The reduction of ar-atlantone selectively affords ar-turmerone, an optically active sesquiterpene obtained from the essential oil of turmeric. Computational studies (DFT calculation) revealed the transition state of this reaction.
References: (1) J. Org. Chem. 2019, 84, 11458–11473. (2) Introduced in Organic Chemistry Portal.
3. Activation of Boron Reagents by Tartaric Acid Derivatives
We have discovered that O-monoacyltartaric acid (MAT catalyst) catalyzes asymmetric conjugate addition of boronic acids or a diboron to α,β-unsaturated ketones (see the figure below, ref. 1). Addition of a urea derivative as a co-catalyst can reduce the amount of catalyst. Kinetic studies were conducted to reveal the mechanism (ref. 2).
References: (1) J. Synth. Org. Chem., Jpn. 2018, 76, 596–603. (2) Org. Lett. 2020, 22, 3780–3784.
4. Selective Monoacylation of Diols
Aiming for efficient synthesis of the above-mentioned MAT catalysts, we have investigated acylation of diols based on activation of 2-pyridyl esters by metal catalysts (see figure below). As a result, higly enantioselective desymmetrization of meso-tartaric acid diesters by acylation has been achieved for the first time (ref. 1).
References: (1) J. Org. Chem. 2019, 84, 9313–9321.
5. Search for Pharmaceutical Seeds
Some compounds synthesized by the reaction developed in our laboratory were found to have neuroprotective effect on dopaminergic neurons (ref. 1, 2, collaboration with Prof. Takahiro Seki, Himeji Dokkyo University) and antiviral activity (ref. 3, collaboration with Prof. Masayuki Amano, Kumamoto University). Based on these findings, we aim to elucidate the molecular mechanism and improve biological activity through organic synthesis.
References: (1) Cells 2021, 10, 1090. (2) press release. (3) ACS Omega 2023, 8, 1369–1374.
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