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Volumn 16, Issue 3, 2010, Pages 141-147

Selective cleavage of an azaGly peptide bond by copper(II). Long-range effect of histidine residue

Author keywords

Azaglycine; Azapeptides; Cleavage; Cu(II); Histidine; Long range effect

Indexed keywords

AZAPEPTIDE; CUPRIC ION; FERRIC ION; FERROUS ION; GLYCINE; HISTIDINE; PALLADIUM; PEPTIDE DERIVATIVE; PLATINUM; UNCLASSIFIED DRUG;

EID: 76749107976     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1211     Document Type: Article
Times cited : (10)

References (41)
  • 1
    • 0013906264 scopus 로고
    • Peptide and azapeptide synthesis by means of a new N-activated amino acid derivative
    • Gante J. Peptide and azapeptide synthesis by means of a new N-activated amino acid derivative. Chem. Ber. 1966; 99: 1576-1579.
    • (1966) Chem. Ber , vol.99 , pp. 1576-1579
    • Gante, J.1
  • 3
    • 33750739736 scopus 로고    scopus 로고
    • The beta-turn scaffold of tripeptide containing an azaphenylalanine residue
    • Lee HJ, Park HM, Lee KB. The beta-turn scaffold of tripeptide containing an azaphenylalanine residue. Biophys. Chem. 2007; 125: 117-126.
    • (2007) Biophys. Chem , vol.125 , pp. 117-126
    • Lee, H.J.1    Park, H.M.2    Lee, K.B.3
  • 6
    • 0017026344 scopus 로고
    • Synthesis and biological activity of alpha-azapeptides: Alpha-aza-analogues of luteinizing hormone releasing hormone
    • Dutta AS, Furr BJ, Giles MB, Morley JS. Synthesis and biological activity of alpha-azapeptides: alpha-aza-analogues of luteinizing hormone releasing hormone. Clin. Endocrinol. (Oxf) 1976; 5: (Suppl): 291S-298S.
    • (1976) Clin. Endocrinol. (Oxf) , vol.5 , Issue.SUPPL.
    • Dutta, A.S.1    Furr, B.J.2    Giles, M.B.3    Morley, J.S.4
  • 7
    • 0025957802 scopus 로고
    • Inhibition of trypsin by t-butyloxycarbonyl-alpha-aza-(4-aminophenyl)alanine phenyl ester
    • Din H, Gray CJ, Ireson JC, McDonald R. Inhibition of trypsin by t-butyloxycarbonyl-alpha-aza-(4-aminophenyl)alanine phenyl ester. J. Chem. Technol. Biotechnol. 1991; 50: 181-189.
    • (1991) J. Chem. Technol. Biotechnol , vol.50 , pp. 181-189
    • Din, H.1    Gray, C.J.2    Ireson, J.C.3    McDonald, R.4
  • 9
    • 33745314454 scopus 로고    scopus 로고
    • Novel aza peptide inhibitors and active-site probes of papain-family cysteine proteases
    • Verhelst SH, Witte MD, Arastu-Kapur S, Fonovic M, Bogyo M. Novel aza peptide inhibitors and active-site probes of papain-family cysteine proteases. ChemBioChem 2006; 7: 943-950.
    • (2006) ChemBioChem , vol.7 , pp. 943-950
    • Verhelst, S.H.1    Witte, M.D.2    Arastu-Kapur, S.3    Fonovic, M.4    Bogyo, M.5
  • 10
    • 0038754759 scopus 로고    scopus 로고
    • Design of selective peptidomimetic agonists for the human orphan receptor BRS-3
    • Weber D, Berger C, Eickelmann P, Antel J, Kessler H. Design of selective peptidomimetic agonists for the human orphan receptor BRS-3. J. Med. Chem. 2003; 46: 1918-1930.
    • (2003) J. Med. Chem , vol.46 , pp. 1918-1930
    • Weber, D.1    Berger, C.2    Eickelmann, P.3    Antel, J.4    Kessler, H.5
  • 12
    • 0030272288 scopus 로고    scopus 로고
    • Synthesis of chemoreversible prodrugs of ara-C with variable time-release profiles. Biological evaluation of their apoptotic activity
    • Wipf P, Li W, Adeyeye CM, Rusnak JM, Lazo JS. Synthesis of chemoreversible prodrugs of ara-C with variable time-release profiles. Biological evaluation of their apoptotic activity. Bioorg. Med. Chem. 1996; 4: 1585-1596.
    • (1996) Bioorg. Med. Chem , vol.4 , pp. 1585-1596
    • Wipf, P.1    Li, W.2    Adeyeye, C.M.3    Rusnak, J.M.4    Lazo, J.S.5
  • 13
    • 0034697540 scopus 로고    scopus 로고
    • Solid phase synthesis of azapeptides utilising reversible amide bond protection to prevent hydantoin formation
    • Liley M, Johnson T. Solid phase synthesis of azapeptides utilising reversible amide bond protection to prevent hydantoin formation. Tetrahedron Lett. 2000; 41: 3983-3985.
    • (2000) Tetrahedron Lett , vol.41 , pp. 3983-3985
    • Liley, M.1    Johnson, T.2
  • 14
    • 2542530630 scopus 로고    scopus 로고
    • Aza-amino acid scan for rapid identification of secondary structure based on the application of N-Boc-aza(1)-dipeptides in peptide synthesis
    • Melendez RE, Lubell WD. Aza-amino acid scan for rapid identification of secondary structure based on the application of N-Boc-aza(1)-dipeptides in peptide synthesis. J. Am. Chem. Soc. 2004; 126: 6759-6764.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 6759-6764
    • Melendez, R.E.1    Lubell, W.D.2
  • 15
    • 28244437082 scopus 로고    scopus 로고
    • Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with fmoc chemistry and aza-amino acids with heteroatomic side chains
    • Boeglin D, Lubell WD. Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with fmoc chemistry and aza-amino acids with heteroatomic side chains. J. Comb. Chem. 2005; 7: 864-878.
    • (2005) J. Comb. Chem , vol.7 , pp. 864-878
    • Boeglin, D.1    Lubell, W.D.2
  • 16
    • 67650693017 scopus 로고    scopus 로고
    • Silver-catalyzed azaGly ligation. Application to the synthesis of azapeptides and of lipid-peptide conjugates
    • Ollivier N, Besret S, Blanpain A, Melnyk O. Silver-catalyzed azaGly ligation. Application to the synthesis of azapeptides and of lipid-peptide conjugates. Bioconjug. Chem. 2009; 20: 1397-1403.
    • (2009) Bioconjug. Chem , vol.20 , pp. 1397-1403
    • Ollivier, N.1    Besret, S.2    Blanpain, A.3    Melnyk, O.4
  • 17
    • 61749092875 scopus 로고    scopus 로고
    • Thiocarbamate-linked peptides by chemoselective peptide ligation
    • Besret S, Ollivier N, Blanpain A, Melnyk O. Thiocarbamate-linked peptides by chemoselective peptide ligation. J. Pept. Sci. 2008; 14: 1244-1250.
    • (2008) J. Pept. Sci , vol.14 , pp. 1244-1250
    • Besret, S.1    Ollivier, N.2    Blanpain, A.3    Melnyk, O.4
  • 18
    • 0025095792 scopus 로고
    • Site-specific oxidation of angiotensin I by copper(II) and L-ascorbate: Conversion of histidine residues to 2-imidazolones
    • Uchida K, Kawakishi S. Site-specific oxidation of angiotensin I by copper(II) and L-ascorbate: conversion of histidine residues to 2-imidazolones. Arch. Biochem. Biophys. 1990; 283: 20-26.
    • (1990) Arch. Biochem. Biophys , vol.283 , pp. 20-26
    • Uchida, K.1    Kawakishi, S.2
  • 19
    • 0027368195 scopus 로고
    • 2-Oxo-histidine as a novel biological marker for oxidatively modified proteins
    • Uchida K, Kawakishi S. 2-Oxo-histidine as a novel biological marker for oxidatively modified proteins. FEBS Lett. 1993; 332: 208-210.
    • (1993) FEBS Lett , vol.332 , pp. 208-210
    • Uchida, K.1    Kawakishi, S.2
  • 21
    • 0029781364 scopus 로고    scopus 로고
    • Specific cleavage of histidine-containing peptides by copper(II)
    • Allen G, Campbell RO. Specific cleavage of histidine-containing peptides by copper(II). Int. J. Pept. Protein Res. 1996; 48: 265-273.
    • (1996) Int. J. Pept. Protein Res , vol.48 , pp. 265-273
    • Allen, G.1    Campbell, R.O.2
  • 24
    • 0038239297 scopus 로고    scopus 로고
    • Combined use of platinum(II) complexes and palladium(II) complexes for selective cleavage of peptides and proteins
    • Milovic NM, Dutca LM, Kostic NM. Combined use of platinum(II) complexes and palladium(II) complexes for selective cleavage of peptides and proteins. Inorg. Chem. 2003; 42: 4036-4045.
    • (2003) Inorg. Chem , vol.42 , pp. 4036-4045
    • Milovic, N.M.1    Dutca, L.M.2    Kostic, N.M.3
  • 25
    • 0037203125 scopus 로고    scopus 로고
    • Interplay of terminal amino group and coordinating side chains in directing regioselective cleavage of natural peptides and proteins with palladium(II) complexes
    • Milovic NM, Kostic NM. Interplay of terminal amino group and coordinating side chains in directing regioselective cleavage of natural peptides and proteins with palladium(II) complexes. Inorg. Chem. 2002; 41: 7053-7063.
    • (2002) Inorg. Chem , vol.41 , pp. 7053-7063
    • Milovic, N.M.1    Kostic, N.M.2
  • 26
    • 0036569574 scopus 로고    scopus 로고
    • Palladium(II) complexes, as synthetic peptidases, regioselectively cleave the second peptide bond "upstream" from methionine and histidine side chains
    • Milovic NM, Kostic NM. Palladium(II) complexes, as synthetic peptidases, regioselectively cleave the second peptide bond "upstream" from methionine and histidine side chains. J. Am. Chem. Soc. 2002; 124: 4759-4769.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 4759-4769
    • Milovic, N.M.1    Kostic, N.M.2
  • 27
    • 0037460193 scopus 로고    scopus 로고
    • Palladium(II) complex as a sequence-specific peptidase: Hydrolytic cleavage under mild conditions of X-Pro peptide bonds in X-Pro-Met and X-Pro-His segments
    • Milovic NM, Kostic NM. Palladium(II) complex as a sequence-specific peptidase: hydrolytic cleavage under mild conditions of X-Pro peptide bonds in X-Pro-Met and X-Pro-His segments. J. Am. Chem. Soc. 2003; 125: 781-788.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 781-788
    • Milovic, N.M.1    Kostic, N.M.2
  • 28
    • 49949124623 scopus 로고
    • Some copper(II) complexes of semicarbazide
    • Campbell MJ, Grzeskowiak R. Some copper(II) complexes of semicarbazide. J. Inorg. Nucl. Chem. 1968; 30: 1865-1871.
    • (1968) J. Inorg. Nucl. Chem , vol.30 , pp. 1865-1871
    • Campbell, M.J.1    Grzeskowiak, R.2
  • 29
    • 37049115956 scopus 로고
    • Azoalkane synthesis by direct oxidation of semicarbazides with copper halide
    • Heyman M, Bandurco VT, Snyder JP. Azoalkane synthesis by direct oxidation of semicarbazides with copper halide. Chem. Commun. 1971; 297-298.
    • (1971) Chem. Commun , pp. 297-298
    • Heyman, M.1    Bandurco, V.T.2    Snyder, J.P.3
  • 30
    • 49349133498 scopus 로고
    • Coordination compounds of hydrazine derivatives with transition metals-IX. The reaction of 1-semicarbazide with copper(II) salts
    • El-Dessouky MA, Amira MF, Abu El Amayem MS, Iskander MF. Coordination compounds of hydrazine derivatives with transition metals-IX. The reaction of 1-semicarbazide with copper(II) salts. J. Inorg. Nucl. Chem. 1976; 38: 463-469.
    • (1976) J. Inorg. Nucl. Chem , vol.38 , pp. 463-469
    • El-Dessouky, M.A.1    Amira, M.F.2    Abu El Amayem, M.S.3    Iskander, M.F.4
  • 31
    • 2542623374 scopus 로고
    • N-Ferrocenylcarbonyl-N′-benzoyhydrazine and its transition metal(II) complexes
    • Qing-bao S, Zhong-lin L, Xiao-liW, Yong-xiang M. N-Ferrocenylcarbonyl-N′-benzoyhydrazine and its transition metal(II) complexes. Transition Met. Chem. 1994; 19: 503-505.
    • (1994) Transition Met. Chem , vol.19 , pp. 503-505
    • Qing-bao, S.1    Zhong-lin, L.2    liW, X.3    Yong-xiang, M.4
  • 32
    • 0025818115 scopus 로고
    • Synthesis and application of Fmoc-hydrazine for the quantitative determination of saccharides by reversed-phase high-performance liquid chromatography in the low and subpicomole range
    • Zhang RE, Cao YL, Hearn MW. Synthesis and application of Fmoc-hydrazine for the quantitative determination of saccharides by reversed-phase high-performance liquid chromatography in the low and subpicomole range. Anal. Biochem. 1991; 195: 160-167.
    • (1991) Anal. Biochem , vol.195 , pp. 160-167
    • Zhang, R.E.1    Cao, Y.L.2    Hearn, M.W.3
  • 33
    • 0025232814 scopus 로고
    • Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids
    • Fields GB, Noble RL. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 1990; 35: 161-214.
    • (1990) Int. J. Pept. Protein Res , vol.35 , pp. 161-214
    • Fields, G.B.1    Noble, R.L.2
  • 34
    • 85046938967 scopus 로고
    • Oxidation and synthetic uses of hydrazo, azo and azoxy compounds
    • Patai S ed, John Wiley: London
    • Newbold BT. Oxidation and synthetic uses of hydrazo, azo and azoxy compounds. In The Chemistry of the Hydrazo, Azo and Azoxy Groups, Patai S (ed.). John Wiley: London, 1975; 541-597.
    • (1975) The Chemistry of the Hydrazo, Azo and Azoxy Groups , pp. 541-597
    • Newbold, B.T.1
  • 35
    • 0032563916 scopus 로고    scopus 로고
    • Aryl hydrazides as linkers for solid phase synthesis which are cleavableunder mild oxidative conditions
    • Millington CR, Quarrell R, Lowe G. Aryl hydrazides as linkers for solid phase synthesis which are cleavableunder mild oxidative conditions. Tetrahedron Lett. 1998; 39: 7201-7204.
    • (1998) Tetrahedron Lett , vol.39 , pp. 7201-7204
    • Millington, C.R.1    Quarrell, R.2    Lowe, G.3
  • 37
    • 0033813880 scopus 로고    scopus 로고
    • Determination of hydrazides and 1,2-diacylhydrazines of aliphatic carboxylic acids by conductometric titration
    • Radushev AV, Chekanova LG, Gusev VY, Sazonova EA. Determination of hydrazides and 1,2-diacylhydrazines of aliphatic carboxylic acids by conductometric titration. J. Anal. Chem. 2000; 55: 445-448.
    • (2000) J. Anal. Chem , vol.55 , pp. 445-448
    • Radushev, A.V.1    Chekanova, L.G.2    Gusev, V.Y.3    Sazonova, E.A.4
  • 38
    • 0029132871 scopus 로고
    • On the pH dependence of amide proton exchange rates in proteins
    • Eriksson MA, Hard T, Nilsson L. On the pH dependence of amide proton exchange rates in proteins. Biophys. J. 1995; 69: 329-339.
    • (1995) Biophys. J , vol.69 , pp. 329-339
    • Eriksson, M.A.1    Hard, T.2    Nilsson, L.3
  • 40
    • 0037254403 scopus 로고    scopus 로고
    • Computational studies of Cu(II)[peptide] binding motifs: Cu[HGGG] and Cu[HG] as models for Cu(II) binding to the prion protein octarepeat region
    • Pushie MJ, Rauk A. Computational studies of Cu(II)[peptide] binding motifs: Cu[HGGG] and Cu[HG] as models for Cu(II) binding to the prion protein octarepeat region. J. Biol. Inorg. Chem. 2003; 8: 53-65.
    • (2003) J. Biol. Inorg. Chem , vol.8 , pp. 53-65
    • Pushie, M.J.1    Rauk, A.2
  • 41
    • 33947348659 scopus 로고
    • The biuret reactions of the hexapeptide, pentaglycylglycine, and of the heptapeptide, hexaglycylglycine
    • Saurwein J. The biuret reactions of the hexapeptide, pentaglycylglycine, and of the heptapeptide, hexaglycylglycine. J. Am. Chem. Soc. 1937; 59: 2177-2178.
    • (1937) J. Am. Chem. Soc , vol.59 , pp. 2177-2178
    • Saurwein, J.1


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