タンパク質有機化学研究室

出版物リスト

川上　徹

  • K. Yamanegi, T. Kawakami, N. Yamada, S. Kumanishi, H. Futani, K. Nakasho, H. Nishiura, The roles of a ribosomal protein S19 polymer in a mouse model of carrageenan-induced acute pleurisy. Immunobiol. 2017, 222, 738-750.
  • Y. Asahina, T. Kawakami, H. Hojo. One-pot native chemical ligation by combination of two orthogonal thioester precursors. Chem. Commun., 53, 2114 (2017). DOI:10.1039/c6cc10243c
  • H. Nishiura, T. Kawakami, M. Kawabe, N. Kato-Kogoe, N. Yamada, K. Nakasho, K. Yamanegi, RP S19 C-terminal peptide trimer acts as a C5 areceptor antagonist. Biochem. Biophys. Reports 2016, 7, 70-76.
  • T. Kawakami, Y. Mishima, M. Kinoshita, Y.-H. Lee, I. Suetake, A thiirane linker for isopeptide mimetics by peptide ligation. Tetrahedron Lett. 2016,57, 2112-2115.
  • T. Hara, A. Tainosyo, T. Kawakami, S. Aimoto, M. Murata, Peptide purification using the chemoselective reaction between N-(methoxy)glycine and isothiocyanato-functionalized resin. J. Pept. Sci. 2016, 22, 379-382.
  • Y. Takechi-Haraya, R. Nadai, H. Kimura, K. Nishitsuji, K. Uchimura, K. Sakai-Kato, K. Kawakami, A. Shigenaga, T. Kawakami, A. Otaka, H. Hojo, N. Sakashita, H. Saito, Enthalpy-driven interactions with sulfated glycosaminoglycans promote cell membrane penetration of arginine peptides. Biochim. Biophys. Acta 2016, 1858, 1339-1349.
  • M. Tanaka, A. Hosotani, Y. Tachibana, M. Nakano, K. Iwasaki, T. Kawakami, T. Mukai. Preparation and characterization of reconstituted lipid-synthetic polymer discoidal particles. Langmuir 2015, 31, 12719-26.
  • Y. Mishima, C. D. Jayasinghe, K. Lu, J. Otani, M. Shirakawa, T. Kawakami, H. Kimura, H. Hojo, P. Carlton, S. Tajima, I. Suetake. Nucleosome compaction facilitates HP1γ binding 1 to methylated H3K9. Nuc. Acids Res. 2015, 43, 10200-10212.
  • T. Hara, E. M. Purwati, A. Tainosyo, T. Kawakami, H. Hojo, S. Aimoto. Site-specific labeling of synthetic peptide using the chemoselective reaction between N-methoxyamino acid and isothiocyanate. J. Pept. Sci. 2015, 21, 765-769.
  • T. Kawakami, R. Yoshikawa, Y. Fujiyoshi, Y. Mishima, H. Hojo, S. Tajima, I. Suetake. Synthesis of histone proteins by CPE ligation using arecombinant peptide as the C-terminal building block. J. Biochem. 2015, 158, 403-411.
  • T. Kawakami. Peptide thioester formation via an intramolecular N to S acyl shift reaction for peptide ligation. Top. Curr. Chem. 2015, 362, 107-135.
  • T. Hara, Y. Huang, A. Ito, T. Kawakami, H. Hojo, M. Murata. Trifluoroethanol-containing RP-HPLC mobile phases for the separation of transmembrane peptides human glycophorin-A, integrin alpha-1, and p24: analysis and prevention of potential side reactions due to formic acid. J. Pept. Sci. 2015, 21, 61-70.
  • H. Suwito, Jumina, Mustofa, P. Pudjiastuti, M. Z. Fanani, Y. Kimata-Ariga, R. Katahira, T. Kawakami, T. Fujiwara, T. Hase, H. M. Sirat, N. N. T. Puspaningsih. Design and synthesis of chalcone derivatives as inhibitors of the ferredoxin - Ferredoxin-NADP+ reductase interaction of Plasmodium falciparum: Pursuing new antimalarial agents. Molecules 2014, 19, 21473-21488.
  • H. Takase, H. Furuchi, M. Tanaka, T. Yamada, K. Matoba, K. Iwasaki, T. Kawakami, T. Mukai. Characterization of reconstituted high-density lipoprotein particles formed by lipid interactions with human serum amyloid A. Biochim. Biophys. Acta 2014, 1841, 1467-1474.
  • T. Kawakami, A. Kamauchi, E. Harada, S. Aimoto. Enhancement in the rate of conversion of peptide Cys-Pro esters to peptide thioesters by structural modification. Tetrahedron Lett. 2014, 55, 79-81.
  • J. Otani, H. Kimura, J. Sharif, T. A. Endo, Y. Mishima, T. Kawakami, H. Koseki, M. Shirakawa, I. Suetake, S. Tajima, Cell cycle-dependent turnover of 5-hydroxymethyl cytosine in mouse embryonic stem cells, PLOS ONE 2013, 8(December 12), e82961/1-11.
  • T. Kawakami, Y. Akai, H. Fujimoto, C. Kita, Y. Aoki, T. Konishi, M. Waseda, L. Takemura, S. Aimoto. Sequential peptide ligation by combining the Cys-Pro ester (CPE) and thioester methods and its application to the synthesis of histone H3 containing a trimethyl lysine residue. Bull. Chem. Soc. Jpn. 2013, 86, 690-697.
  • P. Wei, B.-K. Zheng, P.-R. Guo, T. Kawakami, S.-Z. Luo. The association of polar residues in the DAP12 homodimer: TOXCAT and molecular dynamics simulation studies. Biophys. J. 2013, 104, 1435-1444.
  • M. Tanaka, Y. Takamura, T. Kawakami, S. Aimoto, H. Saito, T. Mukai. Effect of amino acid distribution of amphipathic helical peptide derived from human apolipoprotein A-I on membrane curvature sensing. FEBS Lett. 2013, 587, 510-515.
  • Y. Mishima, M. Watanabe, T. Kawakami, C. D. Jayasinghe, J. Otani, Y. Kikugawa, M. Shirakawa, H. Kimura, O. Nishimura, S. Aimoto, S. Tajima, I. Suetake. Hinge and Chromoshadow of HP1α Participate in Recognition of K9 Methylated Histone H3 in Nucleosomes. J. Mol. Biol. 2013, 425, 54-70.
  • K. Teruya, T. Tanaka, T. Kawakami, K. Akaji, S. Aimoto. Epimerization in peptide thioester condensation. J. Pept. Sci. 2012, 18, 669-677.
  • Y. Takechi, C. Mizuguchi, M. Tanaka, T. Kawakami, S. Aimoto, E. Okamura, H. Saito. Physicochemical mechanism for the lipid membrane binding of polyarginine: The favorable enthalpy change with structural transition from random coil to alfa-helix. Chem. Lett. 2012, 41, 1374-1376.
  • S. Miura, J. Kondo, T. Kawakami, C. Shukunami, S. Aimoto, H. Tanaka, Y. Hiraki. Synthetic disulfide-bridged cyclic peptides mimic the anti-angiogenic actions of chondromodulin-I. Cancer Sci. 2012, 103, 1311-1318.
  • Y. Takechi, H. Yoshii, M. Tanaka, T. Kawakami, S. Aimoto, H. Saito. Physicochemical mechanism for the enhanced ability of lipid membrane penetration of polyarginine. Langmuir 2011, 27, 7099-7107.
  • A. Kitamura, K. Matsui, K. Konoki, N. Matsumori, M. Murata, T. Kawakami, S Aimoto. Lysine proximity significantly affects glycation of lysine-containing collagen model peptides. Bioorg. Med. Chem. 2011, 19, 2125-2129.
  • D. Ozawa, Y. Kaji, H. Yagi, K. Sakurai, T. Kawakami, H. Naiki, Y. Goto. Destruction of amyloid fibrils of keratoepithelin peptides by laser irradiation coupled with amyloid-specific thiofravin T. J. Biol. Chem. 2011, 286, 10856-10863.
  • Y. Todokoro, M. Kobayashi, T. Sato, T. Kawakami, I. Yumen, S. Aimoto, T. Fujiwara, H. Akutsu. Structure analysis of membrane-reconstituted subunit c-ring of E. coli H+-ATP synthase by solid-state NMR. J. Biomol. NMR. 2010, 48, 1-11.
  • H. Yagi, D. Ozawa, K. Sakurai, T. Kawakami, H. Kuyama, O. Nishimura, T. Shimanouchi, R. Kuboi, H. Naiki, Y. Goto. Laser-induced propagation and destruction of amyloid  fibrils. J. Biol. Chem. 2010, 285, 19660-19667.
  • T. Kawakami, S. Shimizu, S. Aimoto. Peptide thioester formation by an N to S acyl Shift reaction at the cysteinyl prolyl cysteine position. Bull. Chem. Soc. Jpn. 2010, 83, 570-574.
  • K. Nakamura, T. Kanao, T. Uesugi, T. Hara, T. Sato, T. Kawakami, S. Aimoto. Synthesis of peptide thioesters via an N-S acyl shift reaction under mild acidic conditions on an N-4,5-dimethoxy-2-mercaptobenzyl auxiliary group. J. Pept. Sci. 2009, 15, 731-737.
  • S. Ohta, M. Tanaka, K. Sakakura, T. Kawakami, S. Aimoto, H. Saito, Defining lipid-binding regions of human serum amyloid A using its fragment peptides. Chem. Phys. Lipids 2009, 162, 62-68.
  • T. Tanaka, M. Tanaka, M. Sugiura, T. Kawakami, S. Aimoto, H. Saito, Deletion of single amino acid E235 affects the structure and lipid interaction of human apolipoprotein A-I C-terminal peptides. Chem. Pharm. Bull. 2009, 57, 499-503.
  • T. Hara, A. Tainosho, K. Nakamura, T. Sato, T. Kawakami, S. Aimoto, Peptide purification by affinity chromatography based on alpha-ketoacyl group chemistry. J. Pept. Sci. 2009, 15, 369-76.
  • T. Kawakami, S. Aimoto, The use of a cysteinyl prolyl ester (CPE) autoactivating unit in peptide ligation reactions. Tetrahedron 2009, 65, 3871-3877.
  • Y. Inaba, T. Kawakami, S. Aimoto, T. Ikegami, T. Takeuchi, T. Nakazawa, S. Yano, Y. Mikata, Preparation and conformational analysis of C-glycosyl beta2- and beta/beta2-peptides. Carbohydrate Res. 2009, 344, 613-626.
  • D. Ozawa, H. Yagi, T. Ban, A. Kameda, T. Kawakami, H. Naiki, Y. Goto, Destruction of amyloid fibrils of a b2-microglobulin fragment by laser beam irradiation. J. Biol. Chem. 2009, 284, 1009-17.
  • M. Tanaka, T. Tanaka, S. Ohta, T. Kawakami, H. Konno, K. Akaji, S. Aimoto, H. Saito, Evaluation of Lipid-Binding Properties of the N-Terminal helical segments in human apolipoprotein A-I using fragment peptides. J. Pept. Sci. 2009, 15, 36-42.
  • W. Liu, J. Z. Fei, T. Kawakami, S. O. Smith, Structural constraints on the transmembrane and juxtamembrane regions of the phospholamban pentamer in membrane bilayers: Gln29 and Leu52. Biochim. Biophys. Acta 2007, 1768, 2971-2978.
  • K. Nakamura, H. Mori, T. Kawakami, H. Hojo, Y. Nakahara, S. Aimoto, Peptide thioester synthesis via an auxiliary-mediated N–S acyl shift reaction in solution. Int. J. Pept. Res. Ther. 2007, 13, 191-202.
  • T. Kawakami, S. Aimoto, Sequential peptide ligation by using a controlled cysteinyl prolyl ester (CPE) autoactivating unit. Tetrahedron Lett. 2007, 48, 1903-1905.
  • T. Kawakami, S. Aimoto, Peptide ligation using a building block having a cysteinyl prolyl ester (CPE) autoactivating unit at the carboxy terminus. Chem. Lett. 2007, 36, 76-77.
  • K. Nakamura, M. Sumida, T. Kawakami, T. Vorherr, S. Aimoto, Generation of an S-Peptide via an N-S Acyl Shift Reaction in a TFA Solution. Bull. Chem. Soc. Jpn. 2006, 79, 1773-1780.
  • T. Kawakami, M. Sumida, K. Nakamura, T. Vorherr, S. Aimoto, Peptide Thioester Preparation Based on an N-S Acyl Shift Reaction Mediated by a Thiol Ligation Auxiliary. Tetrahedron Lett. 2005, 46, 8805-8807.
  • T. Kawakami, M. Tsuchiya, K. Nakamura, S. Aimoto, Sequential peptide chemical ligation by the thioester method and extended chemical ligation, Tetrahedron Lett. 2005, 46, 5533-36.
  • A. Onoda, H. Yamamoto, Y. Yamada, K. Lee, S. Adachi, T.-A. Okamura, K. Yoshizawa-Kumagaye, K. Nakajima, T. Kawakami, S. Aimoto, N. Ueyama, Switching of turn conformation in an aspartate anion peptide fragment by NH - O(-) hydrogen bonds, Biopolymers 2005, 80, 233-48.
  • H. Yamada, T. Sasaki, S. Niwa, T. Oishi, M. Murata, Toru Kawakami, S. Aimoto, Intact glycation end products containing carboxymethyl-lysine and glyoxal lysine dimer obtained from synthetic collagen model, Bioorg Med Chem Lett. 2004, 14, 5677-80.
  • S. Sekine, K. Kataoka, M. Tanaka, H. Nagata, T. Kawakami, K. Akaji, S. Aimoto, S. Shizukuishi, Active domains of salivary statherin on apatitic surfaces for binding to Fusobacterium nucleatum cells, Microbiology 2004, 150, 2373-9.
  • T. Kakudo, S. Chaki, S. Futaki, I. Nakase, K. Akaji, T. Kawakami, K. Maruyama, H. Kamiya, H. Harashima, Transferrin-modified liposomes equipped with a pH-sensitive fusogenic peptide: An artificial viral-like delivery system, Biochemistry 2004, 43, 5618-28.
  • J. K. Bang, K. Hasegawa, T. Kawakami, S. Aimoto, K. Akaji, Synthesis of an olefin-containing cyclic peptide using the solid-phase Horner–Emmons reaction, Tetrahedron Lett. 2004, 45, 99-102.
  • R. Sugioka, S. Shimizu, T. Funatsu, H Tamagawa, Y. Sawa, T. Kawakami, Y. Tsujimoto, BH4-domain peptide from Bcl-xL exerts anti-apoptotic activity in vivo, Oncogene 2003, 22, 8432–40.
  • R. Nishiuchi, O. Murayama, H. Fujiwara, J. Gu, T. Kawakami, S. Aimoto, Y. Wada, K. Sekiguchi, Characterization of the ligand-binding specificities of integrin alfa3beta1 and alfa6beta1 using a panel of purified laminin isoforms containing distinct alfa chains, J. Biochem. 2003, 134, 497-504.
  • T. Kawakami, S. Aimoto, A photoremovable ligation auxiliary for use in polypeptide synthesis, Tetrahedron Lett. 2003, 44, 6059–61.
  • K. Teruya, T. Kawakami, K. Akaji, S. Aimoto, Total synthesis of [L40I, C90A, C109A]-human T-cell leukemia virus type 1 protease, Tetrahedron Lett. 2002, 43, 1487–90.
  • T. Sato, T. Kawakami, K. Akaji, H. Konishi, K. Mochizuki, T. Fujiwara, H. Akutsu, S. Aimoto, Synthesis of a membrane protein with two transmembrane regions, J. Pept. Sci. 2002, 8, 172–80.
  • S.-I. Murahashi, Y. Imada, T. Kawakami, K. Harada, Y. Yonemushi, N. Tomita, Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active beta-amino acids, J. Am. Chem. Soc. 2002, 124, 2888–9.
  • I. Nishimura, T. Uetsuki, K. Kuwako, T. Hara, T. Kawakami, S. Aimoto, K. Yoshikawa, Cell death induced by a caspase-cleaved transmembrane fragment of the Alzheimer amyloid precursor protein, Cell Death Differ. 2002, 9, 199–208.
  • G. V. Kozhukh, Y. Hagihara, T. Kawakami, K. Hasegawa, H. Naiki, Y Goto, Investigation of a peptide responsible for amyloid fibril formation of 2-microglobulin by Achromobacter protease I, J. Biol. Chem. 2002, 277, 1310–5.
  • K. Hasegawa, Y. L. Sha, J. K. Bang, T. Kawakami, K. Akaji, S. Aimoto, Preparation of phosphopeptide thioesters by Fmoc- and Fmoc(2-F)-solid phase synthesis, Lett. Pept. Sci. 2001, 8, 277-84.
  • A. Detken, E. H. Hardy, M. Ernst, M. Kainosho, T. Kawakami, S. Aimoto, B. H. Meier, Methods for sequential resonance assignment in solid, uniformly 13C, 15N labelled peptides: Quantification and application to antamanide, J. Biomol. NMR 2001, 20, 203–21.
  • S. O. Smith, T. Kawakami, W. Liu, M. Ziliox, S. Aimoto, Helical structure of phospholamban in membrane bilayers, J. Mel. Biol. 2001, 313, 1139–48.
  • H. Sonobe, T. Nishimura, M. Sonobe, T. Nakatsuji,R. Yanagihara, T. Kawakami, S. Aimoto, The molt-inhibiting hormone in the American crayfish Procambarus clarkii: Its chemical synthesis and biological activity, Gen. Comp. Endocr. 2001, 121, 196–204.
  • L. Shi, I. Suetake, T. Kawakami, S. Aimoto, S. Tajima, Xenopus eggs express an identical DNA methyltransferase, Dnmt1, to somatic cells, J. Biochem. 2001, 130, 359–66.
  • T. Kawakami, K. Hasegawa, K. Teruya, K. Akaji, M. Horiuchi, F. Inagaki, Y. Kurihara, S. Uesugi, S. Aimoto, Polypeptide synthesis using an expressed peptide as a building block for condensation with a peptide thioester: application to the synthesis of phosphorylated p21Max protein(1–101), J. Pept. Sci. 2001, 7, 474–87.
  • T. Kawakami, K. Akaji, S. Aimoto, Peptide bond formation mediated by 4,5-dimethoxy-2-mercaptobenzylamine after periodate oxidation of the N-terminal serine residue, Org. Lett. 2001, 3, 1403–5.
  • T. Kawakami, H. Ohtake, H. Arakawa, T. Okachi, Y. Imada, S.-I. Murahashi, Asymmetric synthesis of -amino acids by addition of chiral enolates to nitrones via N-acyloxyiminium ions, Bull.Chem. Soc. Jpn. 2000, 73, 2423–44.
  • T. Nakatsuji, H. Keino, K. Tamura, S. Yoshimura, T. Kawakami, S. Aimoto, H. Sonobe, Changes in the amounts of the molt-inhibiting hormone in the sinus glands during the molt cycle of the American crayfish, Procambarus clarkii, Zool. Sci. 2000, 17, 1129–36.
  • T. Kawakami, C. Toda, K. Akaji, T. Nishimura, T. Nakatsuji, M. Sonobe, H. Sonobe, S. Aimoto, Synthesis of a molt-inhibiting hormone of the American crayfish, Procambarus clarkii and determination of the nature of its disulfide linkages, J. Biochem. 2000, 128, 455–61.
  • T. Kawakami, K. Hasegawa, K.Teruya, K. Akaji, M. Horiuchi, F. Inagaki, Y. Kurihara, S. Uesugi, S. Aimoto, Polypeptide synthesis using an expressed peptide as a building block via the thioester method, Tetrahedron Lett. 2000, 41, 2625–8.
  • T. Kawakami, K. Hasegawa, S. Aimoto, Synthesis of a phosphorylated polypeptide by a thioester method, Bull. Chem. Soc. Jpn. 2000, 73, 197-203.
  • T. Kawakami, H. Ohtake, H. Arakawa, T. Okachi, Y. Imada, S.-I. Murahashi, Asymmetric synthesis of -amino acids by addition of chiral enolates to N-acyloxyiminium ions and application for synthesis of optically active 5-substituted 8-methylindlizidines, Org. Lett. 1999, 1, 107–10.
  • M. Mizuno, K. Haneda, R. Iguchi, I. Muramoto, T. Kawakami, S. Aimoto, K. Yamamoto, T. Inazu, Synthesis of a glycopeptide containing oligosaccharides: chemoenzymic synthesis of eel calcitonin analogs having natural N-linked oligosaccharides, J. Am. Chem. Soc. 1999, 121, 284–90.
  • T. Kawakami, H. Ohtake, H. Arakawa, T. Okachi, Y. Imada, S.-I Murahashi, Reversal of diastereoselectivity of the addition of chiral boron and titanium enolates with nitrones via N-acyloxyiminium intermediates. Asymmetric synthesis of diastereomeric alfa-substituted beta-amino acids, Chem. Lett. 1999, 795–6.
  • M. Mizuno, I. Muramoto, T. Kawakami, M. Seike, S. Aimoto, K. Haneda, and T. Inazu, A synthesis of a glycopeptide analog of eel calcitonin, Tetrahedron Lett. 1998, 39, 55–8.
  • X. Li, T. Kawakami, S. Aimoto, Direct preparation of peptide thioesters using an Fmoc solid-phase method, Tetrahedron Lett. 1998, 39, 8669–72.
  • T. Kawakami, S. Yoshimura, S. Aimoto, Synthesis of reaper, a cysteine-containing polypeptide, using a peptide thioester in the presence of silver chloride as an activator, Tetrahedron Lett. 1998, 39, 7901–4.
  • T. Kawakami, S. Aimoto, Condensation of Cys(Acm)-containing peptide segments with silver chloride as an activator of peptide thioesters, Chem. Lett. 1997, 1157–8.
  • T. Kawakami, S. Kogure, S. Aimoto, Synthesis of cysteine-containing polypeptide using a peptide thioester containing a Cys(Acm) residue, Bull. Chem. Soc. Jpn. 1996, 69, 3331–8.
  • S.-I. Murahashi, Y. Imada, M. Kohno, T. Kawakami, Asymmetric 1,3-dipolar cycloaddition of cyclic nitrones to crotonic acid derivatives bearing chiral auxiliaries. Synthesis of optically active alfa-amino acids, (+)-sedridine, and (+)-hygroline, Synlett 1993, 395–6.
  • Y. Imada, T. Saito, T. Kawakami, S.-I. Murahashi, Osmium-catalyzed asymmetric dihydroxylations of olefins using chiral isoxazolidine ligands, Tetrahedron Lett. 1992, 33, 5081-4.
  • （和文）
  • 相本三郎，川上　徹：ペプチドチオエステルの開く新しい蛋白質合成法．バイオサイエンスとインダストリー，56, 11–5 (1998).
  • 川上　徹：ライゲーション法による蛋白質の合成．日本化学会編　第5版　実験化学講座　有機化合物の合成IV.　丸善　pp326-345（2005）．
  • 川上　徹，相本三郎：N-Sアシル基転位反応を用いるペプチドチオエステル合成法の開発．有機合成化学協会誌，70, 166-176 (2012).
  • 川上　徹，相本三郎：システイン残基におけるS-ペプチド体を利用するペプチドライゲーション法の開発．遺伝子医学　MOOK21　最新ペプチド合成技術とその創薬研究への応用．メディカルドゥ　pp76-82 (2012).
  • 北條裕信，川上　徹：ペプチドチオエステルを用いるペプチド縮合．ファインケミカルシリーズ　クリックケミストリー‐基礎から実用まで‐（編）高田十志和，小山靖人，深瀬浩一，シーエムシー出版　pp214-223 (2014).

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