Title:
AMINO ACID HAVING FUNCTIONAL GROUP CAPABLE OF INTERMOLECULAR HYDROGEN BONDING, PEPTIDE COMPOUND CONTAINING SAME AND METHOD FOR PRODUCTION THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/122182
Kind Code:
A1
Abstract:
The present inventor found that the membrane permeability of a peptide compound can be improved by employing at least one amino acid which has a side chain capable of forming an intermolecular hydrogen bond, as one of the amino acids constituting the peptide compound.
Inventors:
MURAOKA TERUSHIGE (JP)
TANAKA SHOTA (JP)
TANAKA SHOTA (JP)
Application Number:
PCT/JP2019/048720
Publication Date:
June 18, 2020
Filing Date:
December 12, 2019
Export Citation:
Assignee:
CHUGAI PHARMACEUTICAL CO LTD (JP)
International Classes:
C07C229/22; C07C235/06; C07C271/22; C07K7/00; C07K11/02; C07K14/00; C40B40/08; C40B40/10
Domestic Patent References:
| WO2018143145A1 | 2018-08-09 | |||
| WO2018225864A1 | 2018-12-13 | |||
| WO2018124162A1 | 2018-07-05 | |||
| WO2016148044A1 | 2016-09-22 | |||
| WO2013100132A1 | 2013-07-04 | |||
| WO2015179823A2 | 2015-11-26 | |||
| WO2013100132A1 | 2013-07-04 |
Other References:
RAFI, SALMA B. ET AL.: "Predicting and improving the Membrane Permeability of Peptidic Small Molecules", JOURNAL OF MEDICINAL CHEMISTRY, vol. 55, 2012, pages 3163 - 3169, XP055498323, DOI: 10.1021/jm201634q
BERND KUHN, PETER MOHR, MARTIN STAHL: "Intramolecular Hydrogen Bonding in Medicinal Chemistry", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 53, no. 6, 25 March 2010 (2010-03-25), US, pages 2601 - 2611, XP055720106, ISSN: 0022-2623, DOI: 10.1021/jm100087s
ALEXANDER ALEX, DAVID S. MILLAN, MANUEL PEREZ, FLORIAN WAKENHUT, GAVIN A. WHITLOCK: "Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space", MEDCHEMCOMM, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 2, no. 7, 1 January 2011 (2011-01-01), United Kingdom, pages 669, XP055720117, ISSN: 2040-2503, DOI: 10.1039/c1md00093d
FUTURE MED. CHEM., vol. 1, 2009, pages 289 - 1310
ANGEW. CHEM., vol. 57, 2018, pages 14414 - 14438
THE PRACTICE OF MEDICINAL CHEMISTRY, vol. 1, pages 87
"Experimental Chemistry Lecture", vol. 5, MARUZEN CO., article "Thermal Measurements and Equilibrium", pages: 460
JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 20, 2014, pages 9699 - 9703
JOURNAL OF ORGANIC CHEMISTRY, vol. 75, 2010, pages 245
J. AM. CHEM. SOC., vol. 121, 1999, pages 6519
"Solid-phase Synthesis Handbook", 1 May 2002, MERCK
SHIMIZU, Y, INOUE, A., TOMARI, Y, SUZUKI, T., YOKOGAWA, T., NISHIKAWA, K., UEDA, T.: "Cell-free translation reconstituted with purified components", NAT. BIOTECHNOL., vol. 19, 2001, pages 751 - 5, XP037163597, DOI: 10.1038/90802
SHIMIZU, YUEDA, T.: "PURE technology", METHODS MOL. BIOL., vol. 607, 2010, pages 11 - 21
JOSEPHSON, K.HARTMAN, MC.SZOSTAK, JW.: "Ribosomal synthesis of unnatural peptides", J. AM. CHEM. SOC., vol. 127, 2005, pages 11727 - 35, XP055236675, DOI: 10.1021/ja0515809
KWON, I ET AL.: "Breaking the degeneracy of the genetic code", J. AM. CHEM. SOC., vol. 125, 2003, pages 7512 - 3
KAWAKAMI, T. ET AL.: "Ribosomal synthesis of polypeptoids and peptoid-peptide hybrids", J. AM. CHEM. SOC., vol. 130, 2008, pages 16861 - 3
KAWAKAMI, T. ET AL.: "Diverse backbone-cyclized peptides via codon reprogramming", NAT. CHEM. BIOL., vol. 5, 2009, pages 888 - 90, XP055143411, DOI: 10.1038/nchembio.259
DEDKOVA LM ET AL.: "Construction of modified ribosomes for incorporation of D-amino acids into proteins", BIOCHEMISTRY, vol. 45, 2006, pages 15541 - 51
DOI Y ET AL.: "Elongation factor Tu mutants expand amino acid tolerance of protein biosynthesis system", JAM CHEM SOC, vol. 129, 2007, pages 14458 - 62
PARK HS ET AL.: "Expanding the genetic code of Escherichia coli with phosphoserine", SCIENCE, vol. 333, 2011, pages 1151 - 4, XP055014139, DOI: 10.1126/science.1207203
ANDERSON, JC.SCHULTZ, PG.: "Adaptation of an orthogonal archaeal leucyl-tRNA and synthetase pair for four-base, amber, and opal suppression", BIOCHEMISTRY, vol. 42, 2003, pages 9598 - 608, XP002479161, DOI: 10.1021/bi034550w
MURAKAMI, H.KOUROUKLIS, D.SUGA, H.: "Using a solid-phase ribozyme aminoacylation system to reprogram the genetic code", CHEM. BIOL., vol. 10, 2003, pages 1077 - 84, XP003013895, DOI: 10.1016/j.chembiol.2003.10.010
KIGA, D.SAKAMOTO, K.KODAMA, K.KIGAWA, T.MATSUDA, T.YABUKI, T.SHIROUZU, M.HARADA, YNAKAYAMA, H.TAKIO, K.: "An engineered Escherichia coli tyrosyl-tRNA synthetase for site-specific incorporation of an unnatural amino acid into proteins in eukaryotic translation and its application in a wheat germ cell-free system", PROC. NATL. ACAD. SCI. USA., vol. 99, 2002, pages 9715 - 20
CHIN, JW.CROPP, TA.ANDERSON, JC.MUKHERJI, M.ZHANG, Z.SCHULTZ, PG.CHIN, JW.: "An expanded eukaryotic genetic code", SCIENCE, vol. 301, 2003, pages 964 - 7
HARTMAN, MCJOSEPHSON, K.SZOSTAK, JW.: "Enzymatic aminoacylation of tRNA with unnatural amino acids", PROC. NATL. ACAD. SCI. USA., vol. 103, 2006, pages 4356 - 61, XP055311246, DOI: 10.1073/pnas.0509219103
SUBTELNY, AO.HARTMAN, MC.SZOSTAK, JW.: "Ribosomal synthesis of N-methyl peptides", J. AM. CHEM. SOC., vol. 130, 2008, pages 6131 - 6, XP055376645, DOI: 10.1021/ja710016v
HECKLER, TG.CHANG, LH.ZAMA, Y.NAKA, T.CHORGHADE, MS.HECHT, SM.: "T4 RNA ligase mediated preparation of novel ''chemically misacylated'' tRNAPheS", BIOCHEMISTRY, vol. 23, 1984, pages 1468 - 73
MURAKAMI, H.BONZAGNI, NJ.SUGA, H.: "Aminoacyl-tRNA synthesis by a resin-immobilized ribozyme", J. AM. CHEM. SOC., vol. 124, 2002, pages 6834 - 5
HASHIMOTO, N., NINOMIYA, K., ENDO, T., SISIDO, M.: "Simple and quick chemical aminoacylation of tRNA in cationic micellar solution under ultrasonic agitation", CHEM. COMMUN. (CAMB, no. 34, 2005, pages 4321 - 3
NINOMIYA, K.MINOHATA, T.NISHIMURA, M.SISIDO, M.: "In situ chemical aminoacylation with amino acid thioesters linked to a peptide nucleic acid", J. AM. CHEM. SOC., vol. 126, 2004, pages 15984 - 9, XP002337183, DOI: 10.1021/ja048200o
ROBERTS RWSZOSTAK JW: "RNA-peptide fusions for the in vitro selection of peptides and proteins", PROC NATL ACAD SCI USA., vol. 94, 1997, pages 12297 - 302, XP002913434, DOI: 10.1073/pnas.94.23.12297
NEMOTO NMIYAMOTO-SATO EHUSIMI Y: "In vitro virus: bonding of mRNA bearing puromycin at the 3'-terminal end to the C-terminal end of its encoded protein on the ribosome in vitro", FEBS LETT, vol. 414, 1997, pages 405 - 8, XP004366358, DOI: 10.1016/S0014-5793(97)01026-0
YAMAGUCHI J, NAIMUDDIN M, BIYANI M, SASAKI T, MACHIDA M, KUBO T, FUNATSU T, HUSIMI Y, NEMOTO N.: "cDNA display: a novel screening method for functional disulfide-rich peptides by solid-phase synthesis and stabilization of mRNA-protein fusions", NUCLEIC ACIDS RES., vol. 37, no. 16, 2009, pages e108, XP008154704, DOI: 10.1093/nar/gkp514
MATTHEAKIS LCBHATT RRDOWER WJ: "An in vitro polysome display system for identifying ligands from very large peptide libraries", PROC NATL ACAD SCI USA., vol. 91, 1994, pages 9022 - 6, XP002043737, DOI: 10.1073/pnas.91.19.9022
REIERSEN HLOBERSLI ILOSET GAHVATTUM ESIMONSEN BSTACY JEMCGREGOR DFITZGERALD KWELSCHOF MBREKKE OH: "Covalent antibody display--an in vitro antibody-DNA library selection system", NUCLEIC ACIDSRES., vol. 33, 2005, pages e10, XP055154764, DOI: 10.1093/nar/gni010
ODEGRIP RCOOMBER DELDRIDGE BHEDERERRKUHLMAN PAULLMAN CFITZGERALD KMCGREGOR D: "CIS display: In vitro selection of peptides from librariesof protein-DNA complexes", PROC NATL ACAD SCI USA., vol. 101, 2004, pages 2806 - 10, XP002364430, DOI: 10.1073/pnas.0400219101
TAWFIK DSGRIFFITHS AD: "Man-made cell-like compartments for molecular evolution", NAT BIOTECHNOL., vol. 16, 1998, pages 652 - 6, XP002669764, DOI: 10.1038/nbt0798-652
CAS, no. 741288-31-3
CAS , no. 6290-03-5
BEILSTEIN, JOURNAL OF ORGANIC CHEMISTRY, vol. 13, 2017, pages 2428 - 2441
JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, no. 4, 1991, pages 1297 - 1301
See also references of EP 3896056A4
BERND KUHN, PETER MOHR, MARTIN STAHL: "Intramolecular Hydrogen Bonding in Medicinal Chemistry", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 53, no. 6, 25 March 2010 (2010-03-25), US, pages 2601 - 2611, XP055720106, ISSN: 0022-2623, DOI: 10.1021/jm100087s
ALEXANDER ALEX, DAVID S. MILLAN, MANUEL PEREZ, FLORIAN WAKENHUT, GAVIN A. WHITLOCK: "Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space", MEDCHEMCOMM, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 2, no. 7, 1 January 2011 (2011-01-01), United Kingdom, pages 669, XP055720117, ISSN: 2040-2503, DOI: 10.1039/c1md00093d
FUTURE MED. CHEM., vol. 1, 2009, pages 289 - 1310
ANGEW. CHEM., vol. 57, 2018, pages 14414 - 14438
THE PRACTICE OF MEDICINAL CHEMISTRY, vol. 1, pages 87
"Experimental Chemistry Lecture", vol. 5, MARUZEN CO., article "Thermal Measurements and Equilibrium", pages: 460
JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 20, 2014, pages 9699 - 9703
JOURNAL OF ORGANIC CHEMISTRY, vol. 75, 2010, pages 245
J. AM. CHEM. SOC., vol. 121, 1999, pages 6519
"Solid-phase Synthesis Handbook", 1 May 2002, MERCK
SHIMIZU, Y, INOUE, A., TOMARI, Y, SUZUKI, T., YOKOGAWA, T., NISHIKAWA, K., UEDA, T.: "Cell-free translation reconstituted with purified components", NAT. BIOTECHNOL., vol. 19, 2001, pages 751 - 5, XP037163597, DOI: 10.1038/90802
SHIMIZU, YUEDA, T.: "PURE technology", METHODS MOL. BIOL., vol. 607, 2010, pages 11 - 21
JOSEPHSON, K.HARTMAN, MC.SZOSTAK, JW.: "Ribosomal synthesis of unnatural peptides", J. AM. CHEM. SOC., vol. 127, 2005, pages 11727 - 35, XP055236675, DOI: 10.1021/ja0515809
KWON, I ET AL.: "Breaking the degeneracy of the genetic code", J. AM. CHEM. SOC., vol. 125, 2003, pages 7512 - 3
KAWAKAMI, T. ET AL.: "Ribosomal synthesis of polypeptoids and peptoid-peptide hybrids", J. AM. CHEM. SOC., vol. 130, 2008, pages 16861 - 3
KAWAKAMI, T. ET AL.: "Diverse backbone-cyclized peptides via codon reprogramming", NAT. CHEM. BIOL., vol. 5, 2009, pages 888 - 90, XP055143411, DOI: 10.1038/nchembio.259
DEDKOVA LM ET AL.: "Construction of modified ribosomes for incorporation of D-amino acids into proteins", BIOCHEMISTRY, vol. 45, 2006, pages 15541 - 51
DOI Y ET AL.: "Elongation factor Tu mutants expand amino acid tolerance of protein biosynthesis system", JAM CHEM SOC, vol. 129, 2007, pages 14458 - 62
PARK HS ET AL.: "Expanding the genetic code of Escherichia coli with phosphoserine", SCIENCE, vol. 333, 2011, pages 1151 - 4, XP055014139, DOI: 10.1126/science.1207203
ANDERSON, JC.SCHULTZ, PG.: "Adaptation of an orthogonal archaeal leucyl-tRNA and synthetase pair for four-base, amber, and opal suppression", BIOCHEMISTRY, vol. 42, 2003, pages 9598 - 608, XP002479161, DOI: 10.1021/bi034550w
MURAKAMI, H.KOUROUKLIS, D.SUGA, H.: "Using a solid-phase ribozyme aminoacylation system to reprogram the genetic code", CHEM. BIOL., vol. 10, 2003, pages 1077 - 84, XP003013895, DOI: 10.1016/j.chembiol.2003.10.010
KIGA, D.SAKAMOTO, K.KODAMA, K.KIGAWA, T.MATSUDA, T.YABUKI, T.SHIROUZU, M.HARADA, YNAKAYAMA, H.TAKIO, K.: "An engineered Escherichia coli tyrosyl-tRNA synthetase for site-specific incorporation of an unnatural amino acid into proteins in eukaryotic translation and its application in a wheat germ cell-free system", PROC. NATL. ACAD. SCI. USA., vol. 99, 2002, pages 9715 - 20
CHIN, JW.CROPP, TA.ANDERSON, JC.MUKHERJI, M.ZHANG, Z.SCHULTZ, PG.CHIN, JW.: "An expanded eukaryotic genetic code", SCIENCE, vol. 301, 2003, pages 964 - 7
HARTMAN, MCJOSEPHSON, K.SZOSTAK, JW.: "Enzymatic aminoacylation of tRNA with unnatural amino acids", PROC. NATL. ACAD. SCI. USA., vol. 103, 2006, pages 4356 - 61, XP055311246, DOI: 10.1073/pnas.0509219103
SUBTELNY, AO.HARTMAN, MC.SZOSTAK, JW.: "Ribosomal synthesis of N-methyl peptides", J. AM. CHEM. SOC., vol. 130, 2008, pages 6131 - 6, XP055376645, DOI: 10.1021/ja710016v
HECKLER, TG.CHANG, LH.ZAMA, Y.NAKA, T.CHORGHADE, MS.HECHT, SM.: "T4 RNA ligase mediated preparation of novel ''chemically misacylated'' tRNAPheS", BIOCHEMISTRY, vol. 23, 1984, pages 1468 - 73
MURAKAMI, H.BONZAGNI, NJ.SUGA, H.: "Aminoacyl-tRNA synthesis by a resin-immobilized ribozyme", J. AM. CHEM. SOC., vol. 124, 2002, pages 6834 - 5
HASHIMOTO, N., NINOMIYA, K., ENDO, T., SISIDO, M.: "Simple and quick chemical aminoacylation of tRNA in cationic micellar solution under ultrasonic agitation", CHEM. COMMUN. (CAMB, no. 34, 2005, pages 4321 - 3
NINOMIYA, K.MINOHATA, T.NISHIMURA, M.SISIDO, M.: "In situ chemical aminoacylation with amino acid thioesters linked to a peptide nucleic acid", J. AM. CHEM. SOC., vol. 126, 2004, pages 15984 - 9, XP002337183, DOI: 10.1021/ja048200o
ROBERTS RWSZOSTAK JW: "RNA-peptide fusions for the in vitro selection of peptides and proteins", PROC NATL ACAD SCI USA., vol. 94, 1997, pages 12297 - 302, XP002913434, DOI: 10.1073/pnas.94.23.12297
NEMOTO NMIYAMOTO-SATO EHUSIMI Y: "In vitro virus: bonding of mRNA bearing puromycin at the 3'-terminal end to the C-terminal end of its encoded protein on the ribosome in vitro", FEBS LETT, vol. 414, 1997, pages 405 - 8, XP004366358, DOI: 10.1016/S0014-5793(97)01026-0
YAMAGUCHI J, NAIMUDDIN M, BIYANI M, SASAKI T, MACHIDA M, KUBO T, FUNATSU T, HUSIMI Y, NEMOTO N.: "cDNA display: a novel screening method for functional disulfide-rich peptides by solid-phase synthesis and stabilization of mRNA-protein fusions", NUCLEIC ACIDS RES., vol. 37, no. 16, 2009, pages e108, XP008154704, DOI: 10.1093/nar/gkp514
MATTHEAKIS LCBHATT RRDOWER WJ: "An in vitro polysome display system for identifying ligands from very large peptide libraries", PROC NATL ACAD SCI USA., vol. 91, 1994, pages 9022 - 6, XP002043737, DOI: 10.1073/pnas.91.19.9022
REIERSEN HLOBERSLI ILOSET GAHVATTUM ESIMONSEN BSTACY JEMCGREGOR DFITZGERALD KWELSCHOF MBREKKE OH: "Covalent antibody display--an in vitro antibody-DNA library selection system", NUCLEIC ACIDSRES., vol. 33, 2005, pages e10, XP055154764, DOI: 10.1093/nar/gni010
ODEGRIP RCOOMBER DELDRIDGE BHEDERERRKUHLMAN PAULLMAN CFITZGERALD KMCGREGOR D: "CIS display: In vitro selection of peptides from librariesof protein-DNA complexes", PROC NATL ACAD SCI USA., vol. 101, 2004, pages 2806 - 10, XP002364430, DOI: 10.1073/pnas.0400219101
TAWFIK DSGRIFFITHS AD: "Man-made cell-like compartments for molecular evolution", NAT BIOTECHNOL., vol. 16, 1998, pages 652 - 6, XP002669764, DOI: 10.1038/nbt0798-652
CAS, no. 741288-31-3
CAS , no. 6290-03-5
BEILSTEIN, JOURNAL OF ORGANIC CHEMISTRY, vol. 13, 2017, pages 2428 - 2441
JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, no. 4, 1991, pages 1297 - 1301
See also references of EP 3896056A4
Attorney, Agent or Firm:
HARUNA, Masao et al. (JP)
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