메뉴 건너뛰기




Volumn 27, Issue 11, 2016, Pages 2592-2596

Butelase-Mediated Ligation as an Efficient Bioconjugation Method for the Synthesis of Peptide Dendrimers

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMERS; PEPTIDES;

EID: 84996721517     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.6b00538     Document Type: Article
Times cited : (41)

References (49)
  • 1
    • 84901047882 scopus 로고    scopus 로고
    • Developments in the field of bioorthogonal bond forming reactions-past and present trends
    • King, M. and Wagner, A. (2014) Developments in the field of bioorthogonal bond forming reactions-past and present trends Bioconjugate Chem. 25, 825-839 10.1021/bc500028d
    • (2014) Bioconjugate Chem. , vol.25 , pp. 825-839
    • King, M.1    Wagner, A.2
  • 2
    • 77949341762 scopus 로고    scopus 로고
    • Advances in Bioconjugation
    • Kalia, J. and Raines, R. T. (2010) Advances in Bioconjugation Curr. Org. Chem. 14, 138-147 10.2174/138527210790069839
    • (2010) Curr. Org. Chem. , vol.14 , pp. 138-147
    • Kalia, J.1    Raines, R.T.2
  • 4
    • 84924565933 scopus 로고    scopus 로고
    • Advances in chemical protein modification
    • Boutureira, O. and Bernardes, G. J. (2015) Advances in chemical protein modification Chem. Rev. 115, 2174-2195 10.1021/cr500399p
    • (2015) Chem. Rev. , vol.115 , pp. 2174-2195
    • Boutureira, O.1    Bernardes, G.J.2
  • 6
    • 33749019097 scopus 로고    scopus 로고
    • A chemical toolkit for proteins - An expanded genetic code
    • Xie, J. and Schultz, P. G. (2006) A chemical toolkit for proteins - an expanded genetic code Nat. Rev. Mol. Cell Biol. 7, 775-782 10.1038/nrm2005
    • (2006) Nat. Rev. Mol. Cell Biol. , vol.7 , pp. 775-782
    • Xie, J.1    Schultz, P.G.2
  • 7
    • 0029787761 scopus 로고    scopus 로고
    • Site-specific protein modification using a ketone handle
    • Cornish, V. W., Hahn, K. M., and Schultz, P. G. (1996) Site-specific protein modification using a ketone handle J. Am. Chem. Soc. 118, 8150-8151 10.1021/ja961216x
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8150-8151
    • Cornish, V.W.1    Hahn, K.M.2    Schultz, P.G.3
  • 8
    • 0141732270 scopus 로고    scopus 로고
    • Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae
    • Deiters, A., Cropp, T. A., Mukherji, M., Chin, J. W., Anderson, J. C., and Schultz, P. G. (2003) Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae J. Am. Chem. Soc. 125, 11782-11783 10.1021/ja0370037
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11782-11783
    • Deiters, A.1    Cropp, T.A.2    Mukherji, M.3    Chin, J.W.4    Anderson, J.C.5    Schultz, P.G.6
  • 10
    • 0034003659 scopus 로고    scopus 로고
    • Efficient incorporation of unsaturated methionine analogues into proteins in vivo
    • van Hest, J. C. M., Kiick, K. L., and Tirrell, D. A. (2000) Efficient incorporation of unsaturated methionine analogues into proteins in vivo J. Am. Chem. Soc. 122, 1282-1288 10.1021/ja992749j
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1282-1288
    • Van Hest, J.C.M.1    Kiick, K.L.2    Tirrell, D.A.3
  • 11
    • 31544475726 scopus 로고    scopus 로고
    • N-terminally PEGylated human interferon-beta-1a with improved pharmacokinetic properties and in vivo efficacy in a melanoma angiogenesis model
    • Baker, D. P., Lin, E. Y., Lin, K., Pellegrini, M., Petter, R. C., Chen, L. L., Arduini, R. M., Brickelmaier, M., Wen, D. Y., and Hess, D. M. et al. 2006, N-terminally PEGylated human interferon-beta-1a with improved pharmacokinetic properties and in vivo efficacy in a melanoma angiogenesis model Bioconjugate Chem. 17, 179-188 10.1021/bc050237q
    • (2006) Bioconjugate Chem. , vol.17 , pp. 179-188
    • Baker, D.P.1    Lin, E.Y.2    Lin, K.3    Pellegrini, M.4    Petter, R.C.5    Chen, L.L.6    Arduini, R.M.7    Brickelmaier, M.8    Wen, D.Y.9    Hess, D.M.10
  • 12
    • 84863012427 scopus 로고    scopus 로고
    • Modification of N-Terminal alpha-Amino Groups of Peptides and Proteins Using Ketenes
    • Chan, A. O. Y., Ho, C. M., Chong, H. C., Leung, Y. C., Huang, J. S., Wong, M. K., and Che, C. M. (2012) Modification of N-Terminal alpha-Amino Groups of Peptides and Proteins Using Ketenes J. Am. Chem. Soc. 134, 2589-2598 10.1021/ja208009r
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 2589-2598
    • Chan, A.O.Y.1    Ho, C.M.2    Chong, H.C.3    Leung, Y.C.4    Huang, J.S.5    Wong, M.K.6    Che, C.M.7
  • 13
    • 0026826660 scopus 로고
    • Site-Directed Conjugation of Nonpeptide Groups to Peptides and Proteins Via Periodate-Oxidation of a 2-Amino Alcohol - Application to Modification at N-Terminal Serine
    • Geoghegan, K. F. and Stroh, J. G. (1992) Site-Directed Conjugation of Nonpeptide Groups to Peptides and Proteins Via Periodate-Oxidation of a 2-Amino Alcohol-Application to Modification at N-Terminal Serine Bioconjugate Chem. 3, 138-146 10.1021/bc00014a008
    • (1992) Bioconjugate Chem. , vol.3 , pp. 138-146
    • Geoghegan, K.F.1    Stroh, J.G.2
  • 14
    • 84918520747 scopus 로고    scopus 로고
    • A phthalimidation protocol that follows protein defined parameters
    • Singudas, R., Adusumalli, S. R., Joshi, P. N., and Rai, V. (2015) A phthalimidation protocol that follows protein defined parameters Chem. Commun. 51, 473-476 10.1039/C4CC08503E
    • (2015) Chem. Commun. , vol.51 , pp. 473-476
    • Singudas, R.1    Adusumalli, S.R.2    Joshi, P.N.3    Rai, V.4
  • 15
    • 84956839369 scopus 로고    scopus 로고
    • Covalent Chemical Ligation Strategy for Mono- and Polyclonal Immunoglobulins at Their Nucleotide Binding Sites
    • Lac, D., Feng, C., Bhardwaj, G., Le, H., Tran, J., Xing, L., Fung, G., Liu, R., Cheng, H., and Lam, K. S. (2016) Covalent Chemical Ligation Strategy for Mono- and Polyclonal Immunoglobulins at Their Nucleotide Binding Sites Bioconjugate Chem. 27, 159-169 10.1021/acs.bioconjchem.5b00574
    • (2016) Bioconjugate Chem. , vol.27 , pp. 159-169
    • Lac, D.1    Feng, C.2    Bhardwaj, G.3    Le, H.4    Tran, J.5    Xing, L.6    Fung, G.7    Liu, R.8    Cheng, H.9    Lam, K.S.10
  • 16
    • 84875850730 scopus 로고    scopus 로고
    • Protein organic chemistry and applications for labeling and engineering in live-cell systems
    • Takaoka, Y., Ojida, A., and Hamachi, I. (2013) Protein organic chemistry and applications for labeling and engineering in live-cell systems Angew. Chem., Int. Ed. 52, 4088-4106 10.1002/anie.201207089
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 4088-4106
    • Takaoka, Y.1    Ojida, A.2    Hamachi, I.3
  • 18
    • 84996756726 scopus 로고    scopus 로고
    • Recent advances in chemoenzymatic bioconjugation methods
    • McFarland, J. M. and Rabuka, D. (2015) Recent advances in chemoenzymatic bioconjugation methods Org. Chem. Insights 5, 7-14 10.4137/OCI.S17957
    • (2015) Org. Chem. Insights , vol.5 , pp. 7-14
    • McFarland, J.M.1    Rabuka, D.2
  • 19
    • 84883183094 scopus 로고    scopus 로고
    • Enzymatic labeling of proteins: Techniques and approaches
    • Rashidian, M., Dozier, J. K., and Distefano, M. D. (2013) Enzymatic labeling of proteins: techniques and approaches Bioconjugate Chem. 24, 1277-1294 10.1021/bc400102w
    • (2013) Bioconjugate Chem. , vol.24 , pp. 1277-1294
    • Rashidian, M.1    Dozier, J.K.2    Distefano, M.D.3
  • 20
    • 84903708926 scopus 로고    scopus 로고
    • Sortagging: A robust and efficient chemoenzymatic ligation strategy
    • Ritzefeld, M. (2014) Sortagging: a robust and efficient chemoenzymatic ligation strategy Chem.-Eur. J. 20, 8516-8529 10.1002/chem.201402072
    • (2014) Chem. - Eur. J. , vol.20 , pp. 8516-8529
    • Ritzefeld, M.1
  • 22
    • 84906318100 scopus 로고    scopus 로고
    • Butelase 1 is an Asx-specific ligase enabling peptide macrocyclization and synthesis
    • Nguyen, G. K. T., Wang, S. J., Qiu, Y. B., Hemu, X., Lian, Y. L., and Tam, J. P. (2014) Butelase 1 is an Asx-specific ligase enabling peptide macrocyclization and synthesis Nat. Chem. Biol. 10, 732-738 10.1038/nchembio.1586
    • (2014) Nat. Chem. Biol. , vol.10 , pp. 732-738
    • Nguyen, G.K.T.1    Wang, S.J.2    Qiu, Y.B.3    Hemu, X.4    Lian, Y.L.5    Tam, J.P.6
  • 23
    • 84948417006 scopus 로고    scopus 로고
    • Butelase-mediated synthesis of protein thioesters and its application for tandem chemoenzymatic ligation
    • Cao, Y., Nguyen, G. K., Tam, J. P., and Liu, C. F. (2015) Butelase-mediated synthesis of protein thioesters and its application for tandem chemoenzymatic ligation Chem. Commun. (Cambridge, U. K.) 51, 17289-17292 10.1039/C5CC07227A
    • (2015) Chem. Commun. (Cambridge, U. K.) , vol.51 , pp. 17289-17292
    • Cao, Y.1    Nguyen, G.K.2    Tam, J.P.3    Liu, C.F.4
  • 24
    • 84955073791 scopus 로고    scopus 로고
    • Site-Specific N-Terminal Labeling of Peptides and Proteins using Butelase 1 and Thiodepsipeptide
    • Nguyen, G. K., Cao, Y., Wang, W., Liu, C. F., and Tam, J. P. (2015) Site-Specific N-Terminal Labeling of Peptides and Proteins using Butelase 1 and Thiodepsipeptide Angew. Chem., Int. Ed. 54, 15694-15698 10.1002/anie.201506810
    • (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 15694-15698
    • Nguyen, G.K.1    Cao, Y.2    Wang, W.3    Liu, C.F.4    Tam, J.P.5
  • 25
    • 84950282620 scopus 로고    scopus 로고
    • Butelase 1: A Versatile Ligase for Peptide and Protein Macrocyclization
    • Nguyen, G. K., Kam, A., Loo, S., Jansson, A. E., Pan, L. X., and Tam, J. P. (2015) Butelase 1: A Versatile Ligase for Peptide and Protein Macrocyclization J. Am. Chem. Soc. 137, 15398-15401 10.1021/jacs.5b11014
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 15398-15401
    • Nguyen, G.K.1    Kam, A.2    Loo, S.3    Jansson, A.E.4    Pan, L.X.5    Tam, J.P.6
  • 26
    • 0036177932 scopus 로고    scopus 로고
    • Peptide dendrimers: Applications and synthesis
    • Sadler, K. and Tam, J. P. (2002) Peptide dendrimers: applications and synthesis Rev. Mol. Biotechnol. 90, 195-229 10.1016/S1389-0352(01)00061-7
    • (2002) Rev. Mol. Biotechnol. , vol.90 , pp. 195-229
    • Sadler, K.1    Tam, J.P.2
  • 27
    • 0023879414 scopus 로고
    • A novel method for producing anti-peptide antibodies. Production of site-specific antibodies to the T cell antigen receptor beta-chain
    • Posnett, D. N., McGrath, H., and Tam, J. P. (1988) A novel method for producing anti-peptide antibodies. Production of site-specific antibodies to the T cell antigen receptor beta-chain J. Biol. Chem. 263, 1719-1725
    • (1988) J. Biol. Chem. , vol.263 , pp. 1719-1725
    • Posnett, D.N.1    McGrath, H.2    Tam, J.P.3
  • 28
    • 0001331728 scopus 로고
    • Synthetic peptide vaccine design: Synthesis and properties of a high-density multiple antigenic peptide system
    • Tam, J. P. (1988) Synthetic peptide vaccine design: synthesis and properties of a high-density multiple antigenic peptide system Proc. Natl. Acad. Sci. U. S. A. 85, 5409-5413 10.1073/pnas.85.15.5409
    • (1988) Proc. Natl. Acad. Sci. U. S. A. , vol.85 , pp. 5409-5413
    • Tam, J.P.1
  • 29
    • 0025771238 scopus 로고
    • Chemically Unambiguous Peptide Immunogen - Preparation, Orientation and Antigenicity of Purified Peptide Conjugated to the Multiple Antigen Peptide System
    • Lu, Y. A., Clavijo, P., Galantino, M., Shen, Z. Y., Liu, W., and Tam, J. P. (1991) Chemically Unambiguous Peptide Immunogen-Preparation, Orientation and Antigenicity of Purified Peptide Conjugated to the Multiple Antigen Peptide System Mol. Immunol. 28, 623-630 10.1016/0161-5890(91)90131-3
    • (1991) Mol. Immunol. , vol.28 , pp. 623-630
    • Lu, Y.A.1    Clavijo, P.2    Galantino, M.3    Shen, Z.Y.4    Liu, W.5    Tam, J.P.6
  • 30
    • 0026083926 scopus 로고
    • A new synthetic functionalized antigen carrier
    • Drijfhout, J. W. and Bloemhoff, W. (1991) A new synthetic functionalized antigen carrier Int. J. Pept. Protein Res. 37, 27-32 10.1111/j.1399-3011.1991.tb00729.x
    • (1991) Int. J. Pept. Protein Res. , vol.37 , pp. 27-32
    • Drijfhout, J.W.1    Bloemhoff, W.2
  • 31
    • 0026483776 scopus 로고
    • A rational design of synthetic peptide vaccine with a built-in adjuvant. A modular approach for unambiguity
    • Defoort, J. P., Nardelli, B., Huang, W., and Tam, J. P. (1992) A rational design of synthetic peptide vaccine with a built-in adjuvant. A modular approach for unambiguity Int. J. Pept. Protein Res. 40, 214-221 10.1111/j.1399-3011.1992.tb00294.x
    • (1992) Int. J. Pept. Protein Res. , vol.40 , pp. 214-221
    • Defoort, J.P.1    Nardelli, B.2    Huang, W.3    Tam, J.P.4
  • 32
    • 0027947767 scopus 로고
    • Synthesis of Peptide Dendrimer
    • Rao, C. and Tam, J. P. (1994) Synthesis of Peptide Dendrimer J. Am. Chem. Soc. 116, 6975-6976 10.1021/ja00094a078
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6975-6976
    • Rao, C.1    Tam, J.P.2
  • 33
    • 0028862141 scopus 로고
    • A synthetic peptide-based polyoxime vaccine construct of high purity and activity
    • Rose, K., Zeng, W. G., Brown, L. E., and Jackson, D. C. (1995) A synthetic peptide-based polyoxime vaccine construct of high purity and activity Mol. Immunol. 32, 1031-1037 10.1016/0161-5890(95)00090-9
    • (1995) Mol. Immunol. , vol.32 , pp. 1031-1037
    • Rose, K.1    Zeng, W.G.2    Brown, L.E.3    Jackson, D.C.4
  • 34
    • 0028947942 scopus 로고
    • Unprotected Peptides as Building-Blocks for Branched Peptides and Peptide Dendrimers
    • Spetzler, J. C. and Tam, J. P. (1995) Unprotected Peptides as Building-Blocks for Branched Peptides and Peptide Dendrimers Int. J. Pept. Protein Res. 45, 78-85 10.1111/j.1399-3011.1995.tb01570.x
    • (1995) Int. J. Pept. Protein Res. , vol.45 , pp. 78-85
    • Spetzler, J.C.1    Tam, J.P.2
  • 35
    • 84876461419 scopus 로고    scopus 로고
    • Influence of conjugation chemistry and B epitope orientation on the immune response of branched peptide antigens
    • Monso, M., de la Torre, B. G., Blanco, E., Moreno, N., and Andreu, D. (2013) Influence of conjugation chemistry and B epitope orientation on the immune response of branched peptide antigens Bioconjugate Chem. 24, 578-585 10.1021/bc300515t
    • (2013) Bioconjugate Chem. , vol.24 , pp. 578-585
    • Monso, M.1    De La Torre, B.G.2    Blanco, E.3    Moreno, N.4    Andreu, D.5
  • 36
    • 58149179420 scopus 로고    scopus 로고
    • Investigation toward multi-epitope vaccine candidates using native chemical ligation
    • Fujita, Y., Moyle, P. M., Hieu, S., Simerska, P., and Toth, I. (2008) Investigation toward multi-epitope vaccine candidates using native chemical ligation Biopolymers 90, 624-632 10.1002/bip.21002
    • (2008) Biopolymers , vol.90 , pp. 624-632
    • Fujita, Y.1    Moyle, P.M.2    Hieu, S.3    Simerska, P.4    Toth, I.5
  • 37
    • 0028933794 scopus 로고
    • Peptide Antibiotics and Their Role in Innate Immunity
    • Boman, H. G. (1995) Peptide Antibiotics and Their Role in Innate Immunity Annu. Rev. Immunol. 13, 61-92 10.1146/annurev.iy.13.040195.000425
    • (1995) Annu. Rev. Immunol. , vol.13 , pp. 61-92
    • Boman, H.G.1
  • 38
    • 0042830450 scopus 로고    scopus 로고
    • Antibacterial peptides: Basic facts and emerging concepts
    • Boman, H. G. (2003) Antibacterial peptides: basic facts and emerging concepts J. Intern. Med. 254, 197-215 10.1046/j.1365-2796.2003.01228.x
    • (2003) J. Intern. Med. , vol.254 , pp. 197-215
    • Boman, H.G.1
  • 39
    • 33947393032 scopus 로고    scopus 로고
    • Antimicrobial peptides: An overview of a promising class of therapeutics
    • Giuliani, A., Pirri, G., and Nicoletto, S. F. (2007) Antimicrobial peptides: an overview of a promising class of therapeutics Cent. Eur. J. Biol. 2, 1-33 10.2478/s11535-007-0010-5
    • (2007) Cent. Eur. J. Biol. , vol.2 , pp. 1-33
    • Giuliani, A.1    Pirri, G.2    Nicoletto, S.F.3
  • 40
    • 79951556373 scopus 로고    scopus 로고
    • Multivalent Antimicrobial Peptides as Therapeutics: Design Principles and Structural Diversities
    • Liu, S. P., Zhou, L., Lakshminarayanan, R., and Beuerman, R. W. (2010) Multivalent Antimicrobial Peptides as Therapeutics: Design Principles and Structural Diversities Int. J. Pept. Res. Ther. 16, 199-213 10.1007/s10989-010-9230-z
    • (2010) Int. J. Pept. Res. Ther. , vol.16 , pp. 199-213
    • Liu, S.P.1    Zhou, L.2    Lakshminarayanan, R.3    Beuerman, R.W.4
  • 42
    • 0034691281 scopus 로고    scopus 로고
    • Design of salt-insensitive glycine-rich antimicrobial peptides with cyclic tricystine structures
    • Tam, J. P., Lu, Y. A., and Yang, J. L. (2000) Design of salt-insensitive glycine-rich antimicrobial peptides with cyclic tricystine structures Biochemistry 39, 7159-7169 10.1021/bi0003487
    • (2000) Biochemistry , vol.39 , pp. 7159-7169
    • Tam, J.P.1    Lu, Y.A.2    Yang, J.L.3
  • 43
    • 0034113230 scopus 로고    scopus 로고
    • Membranolytic selectivity of cystine-stabilized cyclic protegrins
    • Tam, J. P., Wu, C., and Yang, J. L. (2000) Membranolytic selectivity of cystine-stabilized cyclic protegrins Eur. J. Biochem. 267, 3289-3300 10.1046/j.1432-1327.2000.01359.x
    • (2000) Eur. J. Biochem. , vol.267 , pp. 3289-3300
    • Tam, J.P.1    Wu, C.2    Yang, J.L.3
  • 44
    • 84864447533 scopus 로고    scopus 로고
    • AVPpred: Collection and prediction of highly effective antiviral peptides
    • Thakur, N., Qureshi, A., and Kumar, M. (2012) AVPpred: collection and prediction of highly effective antiviral peptides Nucleic Acids Res. 40, 199-204 10.1093/nar/gks450
    • (2012) Nucleic Acids Res. , vol.40 , pp. 199-204
    • Thakur, N.1    Qureshi, A.2    Kumar, M.3
  • 45
    • 0036183822 scopus 로고    scopus 로고
    • Antimicrobial dendrimeric peptides
    • Tam, J. P., Lu, Y. A., and Yang, J. L. (2002) Antimicrobial dendrimeric peptides Eur. J. Biochem. 269, 923-932 10.1046/j.0014-2956.2001.02728.x
    • (2002) Eur. J. Biochem. , vol.269 , pp. 923-932
    • Tam, J.P.1    Lu, Y.A.2    Yang, J.L.3
  • 46
    • 84885142548 scopus 로고    scopus 로고
    • Cationic host defence peptides: Potential as antiviral therapeutics
    • Gwyer Findlay, E., Currie, S. M., and Davidson, D. J. (2013) Cationic host defence peptides: potential as antiviral therapeutics BioDrugs 27, 479-493 10.1007/s40259-013-0039-0
    • (2013) BioDrugs , vol.27 , pp. 479-493
    • Gwyer Findlay, E.1    Currie, S.M.2    Davidson, D.J.3
  • 48
    • 0033569410 scopus 로고    scopus 로고
    • A cyclic antimicrobial peptide produced in primate leukocytes by the ligation of two truncated alpha-defensins
    • Tang, Y. Q., Yuan, J., Osapay, G., Osapay, K., Tran, D., Miller, C. J., Ouellette, A. J., and Selsted, M. E. (1999) A cyclic antimicrobial peptide produced in primate leukocytes by the ligation of two truncated alpha-defensins Science 286, 498-502 10.1126/science.286.5439.498
    • (1999) Science , vol.286 , pp. 498-502
    • Tang, Y.Q.1    Yuan, J.2    Osapay, G.3    Osapay, K.4    Tran, D.5    Miller, C.J.6    Ouellette, A.J.7    Selsted, M.E.8
  • 49
    • 67649199172 scopus 로고    scopus 로고
    • Antimicrobial Action of Prototypic Amphipathic Cationic Decapeptides and Their Branched Dimers
    • Dewan, P. C., Anantharaman, A., Chauhan, V. S., and Sahal, D. (2009) Antimicrobial Action of Prototypic Amphipathic Cationic Decapeptides and Their Branched Dimers Biochemistry 48, 5642-5657 10.1021/bi900272r
    • (2009) Biochemistry , vol.48 , pp. 5642-5657
    • Dewan, P.C.1    Anantharaman, A.2    Chauhan, V.S.3    Sahal, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.