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Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides.

Autor: Hosono Y; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan., Uchida S; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan., Shinkai M; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan., Townsend CE; Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA, 95064, USA., Kelly CN; Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA, 95064, USA., Naylor MR; Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA, 95064, USA., Lee HW; Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA, 95064, USA., Kanamitsu K; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan., Ishii M; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan., Ueki R; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan., Ueda T; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan., Takeuchi K; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan., Sugita M; Department of Computer Science, School of Computing, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan.; Middle-Molecule IT-based Drug Discovery Laboratory (MIDL), Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan., Akiyama Y; Department of Computer Science, School of Computing, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan. akiyama@c.titech.ac.jp.; Middle-Molecule IT-based Drug Discovery Laboratory (MIDL), Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan. akiyama@c.titech.ac.jp., Lokey SR; Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA, 95064, USA. slokey@ucsc.edu., Morimoto J; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan. jmorimoto@chembio.t.u-tokyo.ac.jp., Sando S; Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan. ssando@chembio.t.u-tokyo.ac.jp.; Department of Bioengineering, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan. ssando@chembio.t.u-tokyo.ac.jp.

Publikováno v: Nature communications [Nat Commun] 2023 Mar 17; Vol. 14 (1), pp. 1416. Date of Electronic Publication: 2023 Mar 17.

Identifying the Cellular Target of Cordyheptapeptide A and Synthetic Derivatives.

Autor: Klein VG; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Bray WM; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Wang HY; Department of Cellular and Molecular Pharmacology, University of California, San Francisco, San Francisco, 94158, United States., Edmondson Q; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Schwochert J; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Ono S; Innovative Research Division, Mitsubishi Tanabe Pharma Corporation, Kanagawa 227-0033, Japan., Naylor MR; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Turmon AC; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Faris JH; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States., Okada O; Innovative Research Division, Mitsubishi Tanabe Pharma Corporation, Kanagawa 227-0033, Japan., Taunton J; Department of Cellular and Molecular Pharmacology, University of California, San Francisco, San Francisco, 94158, United States., Lokey RS; Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States.

Publikováno v: ACS chemical biology [ACS Chem Biol] 2021 Aug 20; Vol. 16 (8), pp. 1354-1364. Date of Electronic Publication: 2021 Jul 12.

Conformation and Permeability: Cyclic Hexapeptide Diastereomers.

Autor: Ono S; Modality Laboratories, Innovative Research Division , Mitsubishi Tanabe Pharma Corporation , 1000 Kamoshida-cho, Aoba-ku , Yokohama , Kanagawa 227-0033 , Japan., Naylor MR; Department of Chemistry and Biochemistry , University of California, Santa Cruz , 1156 High Street , Santa Cruz , California 95064 , United States., Townsend CE; Department of Chemistry and Biochemistry , University of California, Santa Cruz , 1156 High Street , Santa Cruz , California 95064 , United States., Okumura C; Modality Laboratories, Innovative Research Division , Mitsubishi Tanabe Pharma Corporation , 1000 Kamoshida-cho, Aoba-ku , Yokohama , Kanagawa 227-0033 , Japan., Okada O; Modality Laboratories, Innovative Research Division , Mitsubishi Tanabe Pharma Corporation , 1000 Kamoshida-cho, Aoba-ku , Yokohama , Kanagawa 227-0033 , Japan., Lokey RS; Department of Chemistry and Biochemistry , University of California, Santa Cruz , 1156 High Street , Santa Cruz , California 95064 , United States.

Publikováno v: Journal of chemical information and modeling [J Chem Inf Model] 2019 Jun 24; Vol. 59 (6), pp. 2952-2963. Date of Electronic Publication: 2019 May 08.