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Volumn 18, Issue 1, 2012, Pages 30-36

On-resin synthesis of novel arginine-isostere peptides bearing substituted amidine headgroups

Author keywords

Amidine; Arginine; Arginine analogs; Combinatorial chemistry; Solid phase synthesis

Indexed keywords

AMIDINE; ARGININE; GUANIDINE; RESIN; THIOAMIDE; TRIFLUOROMETHANESULFONIC ACID;

EID: 84355166583     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1412     Document Type: Article
Times cited : (1)

References (36)
  • 1
    • 70449672389 scopus 로고    scopus 로고
    • Small but powerful: short peptide hormones and their role in autoimmune inflammation
    • Luhder F, Lee DH, Gold R, Stegbauer J, Linker RA. Small but powerful: short peptide hormones and their role in autoimmune inflammation. J. Immunol. 2009; 217: 1-7.
    • (2009) J. Immunol. , vol.217 , pp. 1-7
    • Luhder, F.1    Lee, D.H.2    Gold, R.3    Stegbauer, J.4    Linker, R.A.5
  • 2
    • 0028349156 scopus 로고
    • Nitric oxide synthases in mammals
    • Knowles RG, Moncada S. Nitric oxide synthases in mammals. Biochem. J. 1994; 298: 249-258.
    • (1994) Biochem. J. , vol.298 , pp. 249-258
    • Knowles, R.G.1    Moncada, S.2
  • 4
    • 45749120326 scopus 로고    scopus 로고
    • Cell-penetrating peptides as delivery vehicles for biology and medicine
    • Stewart KM, Horton KL, Kelley SO. Cell-penetrating peptides as delivery vehicles for biology and medicine. Org. Biomol. Chem. 2008; 6: 2242-2255.
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 2242-2255
    • Stewart, K.M.1    Horton, K.L.2    Kelley, S.O.3
  • 5
    • 25144436860 scopus 로고    scopus 로고
    • Poly-L-proline Type II peptide mimics as probes of the active site occupancy requirements of cGMP-dependent protein kinase
    • Zhang R, Nickl CK, Mamai A, Flemer S, Natarajan A, Dostmann WR, Madalengoitia JS. Poly-L-proline Type II peptide mimics as probes of the active site occupancy requirements of cGMP-dependent protein kinase. J. Pept. Res. 2005; 66: 151-159.
    • (2005) J. Pept. Res. , vol.66 , pp. 151-159
    • Zhang, R.1    Nickl, C.K.2    Mamai, A.3    Flemer, S.4    Natarajan, A.5    Dostmann, W.R.6    Madalengoitia, J.S.7
  • 6
    • 0028064948 scopus 로고
    • Approaches toward selective inhibition of nitric oxide synthase
    • Marletta MA. Approaches toward selective inhibition of nitric oxide synthase. J. Med. Chem. 1994; 37: 1899-1907.
    • (1994) J. Med. Chem. , vol.37 , pp. 1899-1907
    • Marletta, M.A.1
  • 8
    • 33845360094 scopus 로고    scopus 로고
    • Arginine mimetic structures in biologically acive antagonists and inhibitors
    • Peterlin-Mašič L. Arginine mimetic structures in biologically acive antagonists and inhibitors. Current Med. Chem. 2006; 13: 3627-3648.
    • (2006) Current Med. Chem. , vol.13 , pp. 3627-3648
    • Peterlin-Mašič, L.1
  • 9
    • 24344449639 scopus 로고    scopus 로고
    • α methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides
    • α methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides. Tetrahedron Lett. 2005; 46: 7007-7009.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 7007-7009
    • Orwig, K.S.1    Dix, T.A.2
  • 10
    • 24944543920 scopus 로고    scopus 로고
    • Synthesis of a hydroxyethylene isostere of the tripeptide Arg-Gly-Leu via a convergent acyl-like radical addition Strategy
    • Jensen CM, Lindsay KB, Andreasen P, Skrydstrup T. Synthesis of a hydroxyethylene isostere of the tripeptide Arg-Gly-Leu via a convergent acyl-like radical addition Strategy. J. Org. Chem. 2005; 70: 7512-7519.
    • (2005) J. Org. Chem. , vol.70 , pp. 7512-7519
    • Jensen, C.M.1    Lindsay, K.B.2    Andreasen, P.3    Skrydstrup, T.4
  • 11
    • 0035929429 scopus 로고    scopus 로고
    • Synthesis of conformationally constrained arginine and ornithine analogues based on the 3-Substituted pyrrolidine framework
    • Mamai A, Hughes NE, Wurthmann A, Madalengoitia JS. Synthesis of conformationally constrained arginine and ornithine analogues based on the 3-Substituted pyrrolidine framework. J. Org. Chem. 2001, 66, 6483-6486.
    • (2001) J. Org. Chem. , vol.66 , pp. 6483-6486
    • Mamai, A.1    Hughes, N.E.2    Wurthmann, A.3    Madalengoitia, J.S.4
  • 13
    • 0033378391 scopus 로고    scopus 로고
    • Strategies and progress towards the ideal orally active thrombin inhibitor
    • Rewinkle JBM, Adang AEP. Strategies and progress towards the ideal orally active thrombin inhibitor. Curr. Pharm. Des. 1999; 5: 1043-1072.
    • (1999) Curr. Pharm. Des. , vol.5 , pp. 1043-1072
    • Rewinkle, J.B.M.1    Adang, A.E.P.2
  • 16
    • 34347386493 scopus 로고    scopus 로고
    • Synthetic routes to N-Pmc-N',N''-disubstituted guanidines via EDCI-mediated guanylation of amines with N-Pmc-N'-substituted thioureas
    • Flemer Jr S, Madalengoitia JS. Synthetic routes to N-Pmc-N′, N''-disubstituted guanidines via EDCI-mediated guanylation of amines with N-Pmc-N'-substituted thioureas. Synthesis 2007; 12: 1848-1860.
    • (2007) Synthesis , vol.12 , pp. 1848-1860
    • Flemer Jr., S.1    Madalengoitia, J.S.2
  • 17
    • 53049104384 scopus 로고    scopus 로고
    • Strategies for the solid-phase diversification of poly-L-proline-Type II peptide mimic scaffolds and peptide scaffolds through guanidinylation
    • Flemer S, Wurthmann A, Mamai A, Madalengoitia JS. Strategies for the solid-phase diversification of poly-L-proline-Type II peptide mimic scaffolds and peptide scaffolds through guanidinylation. J. Org. Chem. 2008; 73: 7593-7602.
    • (2008) J. Org. Chem. , vol.73 , pp. 7593-7602
    • Flemer, S.1    Wurthmann, A.2    Mamai, A.3    Madalengoitia, J.S.4
  • 18
    • 0037458878 scopus 로고    scopus 로고
    • TFA-sensitive arylsulfonylthiourea-assisted synthesis of N,N'-substituted guanidines
    • Li J, Zhang G, Zhang Z, Fan E. TFA-sensitive arylsulfonylthiourea-assisted synthesis of N, N'-substituted guanidines. J. Org. Chem. 2003; 68: 1611-1614.
    • (2003) J. Org. Chem. , vol.68 , pp. 1611-1614
    • Li, J.1    Zhang, G.2    Zhang, Z.3    Fan, E.4
  • 19
    • 53049103191 scopus 로고    scopus 로고
    • G-substituted L-arginine analogues suitable for solid phase peptide synthesis
    • G-substituted L-arginine analogues suitable for solid phase peptide synthesis. J. Org. Chem. 2008; 73: 7849-7851.
    • (2008) J. Org. Chem. , vol.73 , pp. 7849-7851
    • Martin, N.I.1    Liskamp, R.M.J.2
  • 24
    • 0032212754 scopus 로고    scopus 로고
    • Conformationally constrained NO synthase inhibitors: rigid analogs of L-N-iminoethylornithine
    • Eustache J, Grob A, Lam C, Sellier O, Schulz G. Conformationally constrained NO synthase inhibitors: rigid analogs of L-N-iminoethylornithine. Bioorg. Med. Chem. Lett. 1998; 8: 2961-2966.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2961-2966
    • Eustache, J.1    Grob, A.2    Lam, C.3    Sellier, O.4    Schulz, G.5
  • 25
    • 0032510239 scopus 로고    scopus 로고
    • Acetamidine lysine derivative, N-(5(S)-amino-6,7-dihydroxyheptyl)-ethanimidamide dihydrochloride: a highly selective inhibitor of human inducible nitric oxide synthase
    • Hallinan EA, Tsymbalov S, Finnegan PM, Moore WM, Jerome GM, Currie MG, Pitzele BS. Acetamidine lysine derivative, N-(5(S)-amino-6, 7-dihydroxyheptyl)-ethanimidamide dihydrochloride: a highly selective inhibitor of human inducible nitric oxide synthase. J. Med. Chem. 1998; 41: 775-777.
    • (1998) J. Med. Chem. , vol.41 , pp. 775-777
    • Hallinan, E.A.1    Tsymbalov, S.2    Finnegan, P.M.3    Moore, W.M.4    Jerome, G.M.5    Currie, M.G.6    Pitzele, B.S.7
  • 27
    • 84906289702 scopus 로고    scopus 로고
    • Amidines and N-substituted amidines
    • from, Katritzky AR, Taylor RJK (eds). Elsevier: Amsterdam
    • Dunn PJ. Amidines and N-substituted amidines; from Comprehensive Functional Group Transformations II, Katritzky AR, Taylor RJK (eds). Elsevier: Amsterdam, 2005: 655-699.
    • (2005) Comprehensive Functional Group Transformations II , pp. 655-699
    • Dunn, P.J.1
  • 28
    • 0031684916 scopus 로고    scopus 로고
    • The asymmetric synthesis of arginine mimetics: derivatives of (S)-2-, 3- and 4-amidinophenylalanine suitable for incorporation into enzyme inhibitors and/or peptides
    • Kent DR, Cody WL, Doherty AM. The asymmetric synthesis of arginine mimetics: derivatives of (S)-2-, 3- and 4-amidinophenylalanine suitable for incorporation into enzyme inhibitors and/or peptides. J. Pept. Res. 1998; 52: 201-207.
    • (1998) J. Pept. Res. , vol.52 , pp. 201-207
    • Kent, D.R.1    Cody, W.L.2    Doherty, A.M.3
  • 29
    • 0030768740 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of potent thrombin inhibitors: piperazides of 3-amidinophenylalanine
    • Sturzebecher J, Prasa D, Hauptmann J, Vieweg H, Wikstrom P. Synthesis and structure-activity relationships of potent thrombin inhibitors: piperazides of 3-amidinophenylalanine. J. Med. Chem. 1997; 40: 3091-3099.
    • (1997) J. Med. Chem. , vol.40 , pp. 3091-3099
    • Sturzebecher, J.1    Prasa, D.2    Hauptmann, J.3    Vieweg, H.4    Wikstrom, P.5
  • 30
    • 0032502351 scopus 로고    scopus 로고
    • 5-(1-imino-3-butenyl)-L-ornithine: a neuronal isoform selective mechanism-based inactivator of nitric oxide synthase
    • 5-(1-imino-3-butenyl)-L-ornithine: a neuronal isoform selective mechanism-based inactivator of nitric oxide synthase. J. Biol. Chem. 1998; 273: 8882-8889.
    • (1998) J. Biol. Chem. , vol.273 , pp. 8882-8889
    • Babu, B.R.1    Griffith, O.W.2
  • 31
    • 70149110448 scopus 로고    scopus 로고
    • Developing dual and specific inhibitors of dimethylarginine dimethylaminohydrolase-1 and nitric oxide synthase: toward a targeted polypharmacology to control nitric oxide
    • Wang Y, Monzingo AF, Hu S, Schaller TH, Robertus JD, Fast W. Developing dual and specific inhibitors of dimethylarginine dimethylaminohydrolase-1 and nitric oxide synthase: toward a targeted polypharmacology to control nitric oxide. Biochemistry, 2009; 48: 8624-8635.
    • (2009) Biochemistry , vol.48 , pp. 8624-8635
    • Wang, Y.1    Monzingo, A.F.2    Hu, S.3    Schaller, T.H.4    Robertus, J.D.5    Fast, W.6
  • 32
    • 79955807918 scopus 로고    scopus 로고
    • A comprehensive and facile entry into substituted amidines via the condensation of N-Pmc-substituted thioamides with amines using Mukaiyama reagent as a thiophile
    • Flemer S, Madalengoitia JS. A comprehensive and facile entry into substituted amidines via the condensation of N-Pmc-substituted thioamides with amines using Mukaiyama reagent as a thiophile. Synthesis, 2011; 10: 1638-1648.
    • (2011) Synthesis , vol.10 , pp. 1638-1648
    • Flemer, S.1    Madalengoitia, J.S.2
  • 33
    • 30644468689 scopus 로고
    • Über die struktur der thioamide und ihrer derivate, XXX: N-sulfonylthioamide
    • Walter W, Röhr A. Über die struktur der thioamide und ihrer derivate, XXX: N-sulfonylthioamide. Liebigs Ann. Chem. 1975: 41-53.
    • (1975) Liebigs Ann. Chem. , pp. 41-53
    • Walter, W.1    Röhr, A.2
  • 34
    • 0024406806 scopus 로고
    • Isolation and structure of corazonin, a cardioactive peptide from the American cockroach
    • Veenstra JA. Isolation and structure of corazonin, a cardioactive peptide from the American cockroach. FEBS Lett. 1989; 250: 231-234.
    • (1989) FEBS Lett. , vol.250 , pp. 231-234
    • Veenstra, J.A.1
  • 35
    • 0028221601 scopus 로고
    • Side-product formation during cyclization with HBTU on a solid support
    • Story SC, Aldrich JV. Side-product formation during cyclization with HBTU on a solid support. Int. J. Pept. Protein Res. 1994; 43: 292-296.
    • (1994) Int. J. Pept. Protein Res. , vol.43 , pp. 292-296
    • Story, S.C.1    Aldrich, J.V.2
  • 36
    • 0035674965 scopus 로고    scopus 로고
    • History about the discovery of the renin-angiotensin system
    • Basso N, Terragno NA. History about the discovery of the renin-angiotensin system. Hypertension 2001; 38: 1246-1249.
    • (2001) Hypertension , vol.38 , pp. 1246-1249
    • Basso, N.1    Terragno, N.A.2


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