Laboratory of Synthetic Natural Products Chemistry
Laboratory of Synthetic Natural Products Chemistry
Japanese
Research Achievements
2024
Role of mammalian target of rapamycin in the formation and progression of retinopathy of prematurity-like vascular abnormalities in neonatal rats.
Nakano, A.; Morita, A.; Arima, S.; Nagamitsu, T.; Nakahara, T*.
Microvasc. Res. 2024, 152, 104626.
2023
Total synthesis of tanzawaic acid A.
Tanaka, K.; Suzuki, S.; Lee, D.; Arima, S.; Ohte, S.; Ohshiro, T.; Uchida, R.; Tomoda, H.; Nagamitsu, T*.
Tetrahedron 2023, 143, 133556.
Concise syntheses of (–)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane.
Taguchi, H.; Kawaguchi, M.; Nagamitsu, T.;* Ohtawa, M.*
Org. Biomol. Chem. 2023, 21, 6129-6133.
<ChemRxiv preprint>
ケテン中間体を経由するホモプロパルギルアルコールの新規γ-ラクトン化反応
?発見の経緯からその応用まで?
大多和 正樹*
TCIメール 2023, 192, 2-10. (邦文)
One-pot γ-lactonization of homopropargyl alcohol via intramolecular ketene trapping.
?Its discovery, optimization, and application?
Ohtawa, M.*
TCIMAIL 2023, 192, 2-10. (英文)
2022
Comprehensive studies on the synthetic organic chemistry of unique bioactive natural products; total synthesis, drug discovery and development of new reaction.
Ohtawa, M.*
Yakugakuzasshi 2022, 142, 1067-1075.
-Review for the award-
Total syntheses of furopyridones CJ-16,170 and 2-epi-CJ-16,169.
Lee, D.; Tokizaki, T.; Arima, S.; Nagamitsu, T.*
Tetrahedron Lett. 2022, 107, 154095.
Concise syntheses of (–)-11-O-debenzoyltashironin and (–)-bilobalide.
Ohtawa, M*.; Shenvi, R. A.*
J. Synth. Org. Chem. Jpn. 2022, 80, 766-767.
Synthesis and evaluation of habiterpenol analogs.
Konya, M.; Arima, S.; Lee, D.; Ohtawa, M.; Shimoyama, K.; Fukuda, T.; Uchida, R.; Tomoda, H.; Yamaotsu, N.; Tanaka, N.; Nagamitsu, T.*
Chem. Pharm. Bull. 2022, 70, 261-268.
2021
Impairment of endothelium-dependent vasodilator function of retinal blood vessels in adult rats with a history of retinopathy of prematurity.
Mori, A.; Sumida, D.; Kondo, R.; Nakano, A.; Arima, S.; Asano, D.; Morita, A.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
J. Pharm. Sci. 2021, 146, 233-243.
Mixture of clopidogrel bisulfate and magnesium oxide tablets reduces clopidgrel dose administered through a feeding tube.
Aoki, M.*; Naya, M.; Arima, S.; Shinohara, K.; Shibuya, K.; Ohtawa, M.; Nagamitsu, T.; Otori, K.
J. Pharm. Health Care Sci. 2021, 7, 18-25.
One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping.
Yamane, D.+; Tanaka, H.+; Hirata, A.+; Tamura, Y.; Takahashi, D.; Takahashi, Y.; Nagamitsu, T.*; Ohtawa, M.*
Org. Lett. 2021, 23, 2831-2835.
+D.Y., H.T., and A.H. contributed equally.
2020
Pharmacological depletion of retinal neurons prevents vertical angiogenic sprouting without affecting the superficial vascular plexus.
Morita, A.; Yoshizumi, M.; Arima, S.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
Dev. Dyn. 2020, 250, 497-512.
Synthetic and mechanistic interrogation of Ginkgo biloba chemichal space en route to (–)-bilobalide.
Demoret, R. M.; Baker, M. A.; Ohtawa, M.; Chen, S.; Lam, C-C.; Foril, S.; Houk, K. N.; Shenvi, R. A.*
J. Am. Chem. Soc. 2020, 142, 18599-18618.
<ChemRxiv Preprint>
Press release from Scripps Research
The process of revascularization in the neonatal mouse retina following short-term blockade of vascular endothelial growth factor receptors.
Morita, A.; Goko, T.; Matsumura, M.; Asano, D.; Arima, S.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
Cell Tissue Res. 2020, 382, 529-549.
Synthesis and Absolute Configuration of Habiterpenol.
Konya, M.; Shimoyama, K.; Arima, S.; Fukuda, T.; Uchida, R.; Tomoda, H.; Nagamitsu, T.*
Org. Lett. 2020, 22, 5131-5134.
Abnormal vascular phenotypes associated with the timing of interruption of retinal vascular development in rats.
Kondo, R.; Nakano, A.; Asano, D.; Morita, A.; Arima, S.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
Biol. Pharm. Bull. 2020, 43, 859-863.
Repair of DNA damage induced by the novel nucleoside analogue CNDAG through homologous recombination.
Kiu, X.; Jiang, Y.; Nowak, B.; Ichikawa, S.; Ohtawa, M.; Matsuda, A. Plunkett, W.*
Cancer Chemother. Pharmacol. 2020, 85, 661-672.
2019
Changes in components of the neurovascular unit in the retina in a rat model of retinopathy of prematurity.
Nakano, A.; Kondo, R.; Kaneko, Y.; Arima, S.; Asano, D.; Morita, A. Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
Cell Tissue Res. 2020, 379, 473-486.
An unusual extender unit in incorporates into the modular polyketide synthase of scopranones biosynthesis.
Demachi, A.; Uchida, R.; Arima, S.; Nagamitsu, T.; Hashimoto, J.; Komatsu, M.; Kozue, I.; Shin-ya, K.; Tomoda, H.*; Ikeda, H.*
Biochemistry 2019, 58, 5066-5073.
Concise asymmetric synthesis of (–)-bilobalide.
Baker, M. A.; Demoret, R. M.; Ohtawa, M.*; Shenvi, R. A.*
Nature 2019, 575, 643-646.
Nature Japan ハイライト / 日本語要約
Highlighted in Synfacts. / Highlighted in Org. Chem. Highlights.
Press release from Scripps Research
Attenuation of retinal endothelial vasodilator function in a rat model of retinopathy of prematurity.
Nakano, A.; Mori, A.; Arima, S.; Asano, D.; Morita, A.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
Curr. Eye Res. 2019, 44, 1360-1368.
Total synthesis and absolute configuration of simpotentin, a potentiator of amphotericin B activity.
Ohtawa, M.; Shimizu, E.; Saito, A.; Sakamoto, S.; Waki, A.; Kondo, A.; Yagi, A.; Uchida, R.; Tomoda, H.; Nagamitsu, T.*
Org. Lett. 2019, 21, 5596-5599.
Structure-activity relationship studies of atpenin A5 analogs with chemical modification of the side chain moiety.
Ohtawa, M.; Yano, K.; Miyao, A.; Hiura, T.; Sugiyama, K.; Arima, S.; Kita, K.; Omura, S.; Nagamitsu, T.*
Tetrahedron Lett. 2019, 60, 1037-1042.
Total synthesis of 4-epi-atpenin A5 as a potent nematode complex II inhibitor.
Lee, D.; Kondo, H.; Kuwayama, Y.; Takahashi, K.; Arima, S.; Omura, S.; Ohtawa, M.*; Nagamitsu, T.*
Tetrahedron 2019, 75, 3178-3185.
Special issue in honor of Ryan Shenvi's receipt of the 2019 Tetrahedron Young Investigator Award
2018
Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies.
Witkin, J. M.*; Shenvi, R. A.; Li, X.; Gleason, S. D.; Weiss, J.; Morrow, D.; Gatow, J. T.; Wakulchik, M.; Ohtawa, M.; Lu, H-H.; Martinez, M. D.; Schkeryantz, J. M.; Garpenter, T. S.; Cerne, R.
Biochem. Pharm. 2018, 155, 61-70.
Establishment of an abnormal vascular patterning model in the mouse retina.
Morita, A.; Sawada, S.; Mori, A.; Arima, S.; Sakamoto, K.; Nagamitsu, T.; Nakahara, T.*
J. Pharm. Sci. 2018, 136, 177-188.
Design and synthesis of A-ring simplified Pyripyropene A analogs as potent and selective synthetic SOAT2 inhibitors.
Ohtawa, M.+; Arima, S.+; Ichida, N.; Terayama, T.; Ohno, H.; Yamazaki, T.; Ohshiro, T.; Sato, N.; Omura, S.; Tomoda, H.*; Nagamitsu, T.*
ChemMedChem 2018, 13, 411-421.
+M.O. and S.A. contributed equally.
This paper was chosen as the front cover.
2017
Transient Phenotypic Changes in Endothelial Cells and Pericytes in Neonatal Mouse Retina Following Short-term Blockade of Vascular Endothelial Growth Factor Receptors.
Morita, A.; Mori, A.; Arima, S.; Sakamoto, K.; Nagamitsu, T.; Ishii, K.; Nakahara, T.*
Dev. Dyn. 2018, 247, 699-711.
Scopranones with the two atypical scoop-like moieties produced by Streptomyces sp. BYK-11038.
Uchida, R.+; Lee, D.+; Suwa, I.; Ohtawa, M.; Watanabe, N.; Demachi, A.; Ohte, S.; Katagiri, T.; Nagamitsu, T.; Tomoda, H.*
Org. Lett. 2017, 19, 5980-5983.
+R.U. and D.L. contributed equally.
Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside and alkaloid derivatives.
Fujii, H.*; Shimada, N.; Ohtawa, M.; Karaki, F.; Koshizuka, M.; Hayashida, K.; Kamimura, M.; Makino, K.; Nagamitsu, T.; Nagase, H.
Tetrahedron 2017, 73, 5425-5429.
Synthesis of (–)-11-O-debenzoyltashironin: Neurotrophic sesquiterpenes cause hyperexcitation.
Ohtawa, M.; Krambis, M. J.; Cerne, R.; Schkeryantz, J. M.; Witkin, J. M.; Shenvi, R. A.*
J. Am. Chem. Soc. 2017, 139, 9637-9644.
Among the top 20 most read article on J. Am. Chem. Soc. for July 2017.
Highlighted in Organic Chemistry Portal.
Development of a new air-stable structure-simplified nafuredin-γ analog as a potent and selective nematode complex I inhibitor.
Ohtawa, M.+; Arima, S.+; Shimizu, R.; Hanatani, N.; Shimizu, E.; Shiomi, K.; Kita, K.; Omura, S.; Nagamitsu, T.*
J. Antibiot. 2017, 70, 647-654.
+M.O. and S.A. contributed equally.
2016
A delay in vascularization induces abnormal astrocyte proliferlation and migration in the mouse retina.
Morita, A.; Ushikubo, H.; Mori, A.; Arima, S.; Sakamoto, K.; Nagamitsu, T.; Ishii, K.; Nakahara, T.*
Dev. Dyn. 2017, 246, 186-200.
Synthesis and structural revision of cyslabdan.
Ohtawa, M.; Hishinuma, Y.; Takagi, E.; Yamada, T.; Ito, F.; Arima, S.; Uchida, R.; Kim, Y-P.; Omura, S.; Tomoda, H.; Nagamitsu, T.*
Chem. Pharm. Bull. 2016, 64, 1370-1377.
Simplifungin and valsafungins, antifungal antibiotics of fungal origin.
Ishijima, H.; Uchida, R.; Ohtawa, M.; Kondo, A.; Nagai, K.; Shima, K.; Nonaka, K.; Masuma, R.; Iwamoto, S.; Onodera, H.; Nagamitsu, T.; Tomoda, H.*
J. Org. Chem. 2016, 81, 7373-7383.
2015
Biosynthesis of mercapturic acid derivative of the labdane?type diterpene, cyslabdan that potentiates imipenem activity against methicillin?resistant Staphylococcus aureus: cyslabdan is generated by mycothiol?mediated xenobiotic detoxification.
Ikeda, H.*; Shin-ya, K.; Nagamitsu, T.; Tomoda, H.
J. Microbiol. Miotehnol. 2015, 68, 27-34.
New pyripyropene derivatives, highly SOAT2-selective inhibitors, improve hypercholesterolemia and atherosclerosis in atherogenic mouse model.
Ohshiro, T.; Ohtawa, M.; Nagamitsu, T.; Matsuda, D.; Yagyu, H.; Davis, M. A.; Rudel, L. L.; Ishibashi, S.; Tomoda, H.*
J. Pharm. Exp. Ther. 2015, 355, 299-309.
Treatment of mild-pregnant mice with KRN633, an inhibitor of vascular endothelial growth factor receptor tyrosine kinase, induces abnormal retinal vascular patterning in their newborn pups.
Morita, A.; Nakahara, T.*; Abe, N.; Kurauchi, Y.; Mori, A.; Sakamoto, K.; Nagamitsu, T.; Ishii, K.
Birth Defects Res. B Dev. Reprod. Toxicol. 2014, 101, 293-299.
Total synthesis of (+)-clavulatriene A.
Ito, F.; Ohbatake, Y.; Aoyama, S.; Ikeda, T.; Arima, S.; Yamada, Y.; Ikeda, H.; Nagamitsu, T.*
Synthesis 2015, 47, 1348-1355.
Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors.
Ohtawa, M.; Matsunaga, M.; Fukunaga, K.; Shimizu, R.; Shimizu, E.; Arima, S.; Ohmori, J.; Kita, K.; Shiomi, K.; Omura, S.; Nagamitsu, T.*
Bioorg. Med. Chem. 2015, 23, 932-943.
Novel terpenes generated by heterologous expression of bacterial terpene synthase genes in an engineered Streptomyces host.
Yamada, Y.; Arima, S.; Nagamitsu, T.; Johmoto, K.; Uesaka, H.; Eguchi, T.; Shin-ya, K.; Cane, D. E.; Ikeda, H.*
J. Antibiot. 2015, 68, 385-394.
Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives.
Yamamuro, D.; Uchida, R.; Ohtawa, M.; Arima, S.; Futamura, Y.; Katane, K.; Honma, H.; Nagamitsu, T.; Osada, H.; Tomoda, H.*
Bioorg. Med. Chem. 2015, 25, 313-316.
In vitro metabolism of pyripyropene A and ACAT inhibitory activity of its metabolites.
Matsuda, D.; Ohshiro, T.; Ohtawa, M.; Yamazaki, H.; Nagamitsu, T.; Tomoda, H.*
J. Antibiot. 2015, 68, 27-34.