Youhei Sohma

Summary

Affiliation: University of Tokyo
Country: Japan

Publications

  1. doi request reprint Synthesis of O-acyl isopeptides
    Youhei Sohma
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7 3 1, Hongo, Tokyo 113 0033, Japan
    Chem Rec 13:218-23. 2013
  2. doi request reprint Comparative properties of Aβ1-42, Aβ11-42, and [Pyr¹¹]Aβ11-42 generated from O-acyl isopeptides
    Youhei Sohma
    Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem Lett 23:1326-9. 2013
  3. doi request reprint Controlled production of amyloid beta peptide from a photo-triggered, water-soluble precursor "click peptide"
    Atsuhiko Taniguchi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Kyoto, Japan
    Chembiochem 9:3055-65. 2008
  4. ncbi request reprint 'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'
    Atsuhiko Taniguchi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Pept Sci 13:868-74. 2007
  5. ncbi request reprint No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: scope and limitation of O-N intramolecular acyl and acyloxy migration reactions
    Mariusz Skwarczynski
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Med Chem 48:2655-66. 2005
  6. ncbi request reprint The 'O-acyl isopeptide method' for the synthesis of difficult sequence-containing peptides: application to the synthesis of Alzheimer's disease-related amyloid beta peptide (Abeta) 1-42
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Japan
    J Pept Sci 11:441-51. 2005
  7. ncbi request reprint 'Click peptide': a novel 'O-acyl isopeptide method' for peptide synthesis and chemical biology-oriented synthesis of amyloid beta peptide analogues
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412
    J Pept Sci 12:823-8. 2006
  8. ncbi request reprint O-N intramolecular acyl migration reaction in the development of prodrugs and the synthesis of difficult sequence-containing bioactive peptides
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Biopolymers 76:344-56. 2004
  9. ncbi request reprint 'O-Acyl isopeptide method' for the efficient preparation of amyloid beta peptide 1-42 mutants
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem 13:6167-74. 2005
  10. ncbi request reprint Development of O-acyl isopeptide method
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Kyoto, Japan
    Biopolymers 88:253-62. 2007

Collaborators

  • Atsuhiko Taniguchi
  • Hidehito Mukai
  • Shun Hirota
  • Kenichi Akaji
  • Motomu Kanai
  • Taisuke Tomita
  • Hui Wang
  • Hikaru Matsumoto
  • Yoshiaki Kiso
  • Tooru Kimura
  • Taku Yoshiya
  • Hiroyuki Kawashima
  • Mariusz Skwarczynski
  • Yoshio Hayashi
  • Yoshio Hamada
  • Harichandra D Tagad
  • Yohei Seki
  • Masayuki Yamashita
  • Mayo Noguchi
  • Tomomi Kuruma
  • Jeffrey Tri Nguyen
  • Takashi Hamada
  • Yuka Hasegawa
  • Koushi Hidaka
  • Fukue Fukao
  • Naoko Abe
  • Katsumi Matsuzaki
  • Nui Ito
  • Setsuko Nakamura
  • Maiko Kimura
  • Kounosuke Oisaki
  • Daisuke Sasaki
  • Kana Tanabe
  • Hitomi Kitamura
  • Tomoya Nakanishi
  • Wakana Kawamura
  • Ayano Higa
  • Yuki Toda
  • Abdellah Yamani
  • Hamdy Abdel-Rahman
  • Hayato Ikari
  • Ayaka Nagamine
  • Kazuhiro Okamoto
  • Naoto Igawa
  • Takuma Okada
  • Keisuke Ikeda
  • Miho Tsukuda
  • Yousuke Chiyomori
  • Jun Ohtake

Detail Information

Publications33

  1. doi request reprint Synthesis of O-acyl isopeptides
    Youhei Sohma
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7 3 1, Hongo, Tokyo 113 0033, Japan
    Chem Rec 13:218-23. 2013
    ..This O-acyl-isopeptide approach also serves as a means to control the biological function of the peptide in question. Herein, we report the synthesis of O-acyl isopeptides and some of their applications...
  2. doi request reprint Comparative properties of Aβ1-42, Aβ11-42, and [Pyr¹¹]Aβ11-42 generated from O-acyl isopeptides
    Youhei Sohma
    Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem Lett 23:1326-9. 2013
    ....
  3. doi request reprint Controlled production of amyloid beta peptide from a photo-triggered, water-soluble precursor "click peptide"
    Atsuhiko Taniguchi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Kyoto, Japan
    Chembiochem 9:3055-65. 2008
    ....
  4. ncbi request reprint 'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'
    Atsuhiko Taniguchi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Pept Sci 13:868-74. 2007
    ..In non-polar solvents such as CHCl(3) or CH(2)Cl(2), the side reaction was less likely to occur. Using CH(2)Cl(2) as solvent in coupling the unit, the target Abeta1-42 isopeptide was synthesized with almost no major side reaction...
  5. ncbi request reprint No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: scope and limitation of O-N intramolecular acyl and acyloxy migration reactions
    Mariusz Skwarczynski
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Med Chem 48:2655-66. 2005
    ....
  6. ncbi request reprint The 'O-acyl isopeptide method' for the synthesis of difficult sequence-containing peptides: application to the synthesis of Alzheimer's disease-related amyloid beta peptide (Abeta) 1-42
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Japan
    J Pept Sci 11:441-51. 2005
    ....
  7. ncbi request reprint 'Click peptide': a novel 'O-acyl isopeptide method' for peptide synthesis and chemical biology-oriented synthesis of amyloid beta peptide analogues
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412
    J Pept Sci 12:823-8. 2006
    ....
  8. ncbi request reprint O-N intramolecular acyl migration reaction in the development of prodrugs and the synthesis of difficult sequence-containing bioactive peptides
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Biopolymers 76:344-56. 2004
    ..This suggests that our new method based on O-N intramolecular acyl migration is an important method for the synthesis of difficult sequence-containing bioactive peptides...
  9. ncbi request reprint 'O-Acyl isopeptide method' for the efficient preparation of amyloid beta peptide 1-42 mutants
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem 13:6167-74. 2005
    ..These isopeptides provide a new system useful for investigating the biological function of Abeta1-42 mutants...
  10. ncbi request reprint Development of O-acyl isopeptide method
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Kyoto, Japan
    Biopolymers 88:253-62. 2007
    ..As the O-acyl isopeptide method becomes more widely utilized, we have composed this review to facilitate its application for the production of peptides and proteins...
  11. doi request reprint Structure-guided design and synthesis of P1' position 1-phenylcycloalkylamine-derived pentapeptidic BACE1 inhibitors
    Harichandra D Tagad
    Department of Medicinal Chemistry, Centre for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, Japan
    Bioorg Med Chem 19:5238-46. 2011
    ..The most potent inhibitor of this pentapeptide series, KMI-1830, possessing 1-phenylcyclopentylamine at the P1' position had an IC(50) value of 11.6 nM against BACE1 in vitro enzymatic assay...
  12. doi request reprint Design, synthesis, and biophysical properties of a helical Abeta1-42 analog: Inhibition of fibrillogenesis and cytotoxicity
    Katsumi Matsuzaki
    Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo ku, Kyoto 606 8501, Japan
    Biochem Biophys Res Commun 371:777-80. 2008
    ..Thus, our helical Abeta1-42 is not only a model peptide to investigate the role of helical intermediates in fibrillization by Abeta, but also an inhibitor of Abeta-induced cytotoxicity...
  13. ncbi request reprint A new class of aggregation inhibitor of amyloid-β peptide based on an O-acyl isopeptide
    Hiroyuki Kawashima
    Department of Pharmaceutical Manufacturing Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem 21:6323-7. 2013
    ..Inhibition was verified by fluorescence anisotropy, Western blot, and atomic force microscopy. This report suggests a new class of Aβ aggregation inhibitor based on modification of Aβ1-42 at Gly(25)-Ser(26). ..
  14. ncbi request reprint "Click peptide" based on the "o-acyl isopeptide method": control of A beta1-42 production from a photo-triggered A beta1-42 analogue
    Atsuhiko Taniguchi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Am Chem Soc 128:696-7. 2006
    ..This method provides a novel system useful for investigating the dynamic biological functions of Abeta1-42 in AD by inducible activation of Abeta1-42 self-assembly...
  15. ncbi request reprint Development of first photoresponsive prodrug of paclitaxel
    Mariusz Skwarczynski
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science and 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Japan
    Bioorg Med Chem Lett 16:4492-6. 2006
    ..The prodrug was selectively converted to isotaxel by visible light irradiation (430 nm) with the cleavage of coumarin. Finally, paclitaxel was released by subsequent spontaneous O-N intramolecular acyl migration...
  16. ncbi request reprint "O-acyl isopeptide method" for peptide synthesis: synthesis of forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH
    Taku Yoshiya
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Org Biomol Chem 5:1720-30. 2007
    ..The O-acyl isodipeptide units are important building blocks to enable the routine use of the O-acyl isopeptide method...
  17. ncbi request reprint O-N intramolecular acyl migration strategy in water-soluble prodrugs of taxoids
    Mariusz Skwarczynski
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem Lett 13:4441-4. 2003
    ..Both O-N migration and undesired hydrolysis of the Boc group occurred under physiological conditions, although no oxazolidinone formation was observed, suggesting the limitation of our water-soluble prodrug strategy to docetaxel...
  18. ncbi request reprint Development of water-soluble prodrugs of the HIV-1 protease inhibitor KNI-727: importance of the conversion time for higher gastrointestinal absorption of prodrugs based on spontaneous chemical cleavage
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Med Chem 46:4124-35. 2003
    ..The present information is an intriguing discovery and is one of the key factors that will contribute to the future design of practical water-soluble prodrugs...
  19. doi request reprint Self-assembly pathways of E22Δ-type amyloid β peptide mutants generated from non-aggregative O-acyl isopeptide precursors
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Kyoto 607 8412, Japan
    Bioorg Med Chem 19:3787-92. 2011
    ..Additionally, the Aβ1-42(E22Δ) oligomers appear to differ from Aβ1-42(WT) oligomers in size, shape, or both. These results should provide new insights into the functions of Aβ(E22Δ) mutants...
  20. ncbi request reprint "Click peptide": pH-triggered in situ production and aggregation of monomer Abeta1-42
    Atsuhiko Taniguchi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, Japan
    Chembiochem 10:710-5. 2009
    ..This click peptide strategy should provide a reliable experimental system to investigate the pathological role of Abeta1-42 in Alzheimer's disease...
  21. ncbi request reprint O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids
    Mariusz Skwarczynski
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Org Chem 71:2542-5. 2006
    ..Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity...
  22. doi request reprint 'Click peptide' using production of monomer Aβ from the O-acyl isopeptide: application to assay system of aggregation inhibitors and cellular cytotoxicity
    Youhei Sohma
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, Japan
    Bioorg Med Chem 19:1729-33. 2011
    ....
  23. ncbi request reprint Epimerization-free synthesis of cyclic peptide by use of the O-acyl isopeptide method
    Taku Yoshiya
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    J Pept Sci 16:437-42. 2010
    ..The isopeptide was then efficiently converted to the desired cyclic peptide via an O-to-N acyl migration reaction using a silica gel-anchored base...
  24. ncbi request reprint A novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: design and synthesis of isotaxel
    Yoshio Hayashi
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412 Japan
    J Med Chem 46:3782-4. 2003
    ..This prodrug, a 2'-O-benzoyl isoform of paclitaxel, has no additional functional auxiliaries released during conversion to paclitaxel, which would be a great advantage in toxicology and medical economics...
  25. doi request reprint Click Peptide concept: o-acyl isopeptide of islet amyloid polypeptide as a nonaggregative precursor molecule
    Taku Yoshiya
    Kyoto Pharmaceutical University, Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Yamashina ku, Kyoto, Japan
    Chembiochem 12:1216-22. 2011
    ....
  26. doi request reprint S-acyl isopeptide method: use of allyl-type protective group for improved preparation of thioester-containing S-acyl isopeptides by Fmoc-based SPPS
    Taku Yoshiya
    Department of Medicinal Chemistry, Division of Medicinal Chemical Sciences, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Biopolymers 96:228-39. 2011
    ..The S-acyl isopeptide method will be a usefuI method to prepare the difficult sequence-containing peptides with Cys residue...
  27. doi request reprint O-acyl isopeptide method: efficient synthesis of isopeptide segment and application to racemization-free segment condensation
    Taku Yoshiya
    Department of Medicinal Chemistry, Division of Medicinal Chemical Sciences, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, 607 8412, Japan
    Org Biomol Chem 7:2894-904. 2009
    ..We also succeeded in performing the segment condensation in a sequential manner and in solution phase conditions as well...
  28. ncbi request reprint "Click peptides"--chemical biology-oriented synthesis of Alzheimer's disease-related amyloid beta peptide (abeta) analogues based on the "O-acyl isopeptide method"
    Youhei Sohma
    Department of Medicinal Chemistry Center for Frontier Research in Medicinal Science 21st Century COE Program, Kyoto Pharmaceutical University Yamashina ku, Kyoto 607 8412, Japan
    Chembiochem 7:1549-57. 2006
    ..The use of click peptides could be a useful strategy to investigate the biological functions of Abeta1-42 in AD through inducible activation of Abeta1-42 self-assembly...
  29. doi request reprint Design of pentapeptidic BACE1 inhibitors with carboxylic acid bioisosteres at P1' and P4 positions
    Harichandra D Tagad
    Department of Medicinal Chemistry, Centre Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto 607 8412, Japan
    Bioorg Med Chem 18:3175-86. 2010
    ..These inhibitors exhibited improved BACE1 inhibitory activities and a thorough quantitative structure-activity relationship study was performed...
  30. ncbi request reprint Synthesis of an O-acyl isopeptide by using native chemical ligation in an aqueous solvent system
    Hiroyuki Kawashima
    Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, 607 8412, Japan Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, 607 412, Japan
    J Pept Sci 20:361-5. 2014
    ....
  31. ncbi request reprint Serine-selective aerobic cleavage of peptides and a protein using a water-soluble copper-organoradical conjugate
    Yohei Seki
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo ku, Tokyo 113 0033 Japan
    Angew Chem Int Ed Engl 53:6501-5. 2014
    ..Peptides comprising D-amino acids or sensitive disulfide pairs are competent substrates. The system is extendable to the site-selective cleavage of a native protein, ubiquitin, which comprises more than 70 amino acid residues. ..
  32. doi request reprint Attenuation of the aggregation and neurotoxicity of amyloid-β peptides by catalytic photooxygenation
    Atsuhiko Taniguchi
    Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo ku, Tokyo 113 0033 Japan Japan Science and Technology Agency JST, ERATO, Kanai Life Science Catalysis Project, Bunkyo ku, Tokyo 113 0033 Japan
    Angew Chem Int Ed Engl 53:1382-5. 2014
    ..Furthermore, oxygenated Aβ1-42 inhibited the aggregation and cytotoxicity of native Aβ. ..
  33. ncbi request reprint New water-soluble prodrugs of HIV protease inhibitors based on O-->N intramolecular acyl migration
    Yoshio Hamada
    Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina ku, Kyoto, Japan
    Bioorg Med Chem 10:4155-67. 2002
    ..In contrast to the prodrugs 3, 4, 6, and 7, the prodrug 12 was very slowly converted to ritonavir probably through a six-membered ring intermediate, with the t(1/2) value of 32h that may not be suitable for practical use...