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Volumn 55, Issue 1, 2012, Pages 64-69

Chemical synthesis of a cyclotide via intramolecular cyclization of peptide O-esters

Author keywords

chemical synthesis; cyclotides; macrolactamization; native chemical ligation; peptide O ester

Indexed keywords

AMINO ACID RESIDUES; BIOLOGICAL ACTIVITIES; CHEMICAL SYNTHESIS; CIRCULAR PROTEINS; CYCLOTIDES; ENZYMATIC STABILITY; INTRAMOLECULAR CYCLIZATIONS; MACROLACTAMIZATION; NATIVE CHEMICAL LIGATION; OXIDATIVE REFOLDING; PHARMACEUTICAL APPLICATIONS; SOLID PHASE PEPTIDE SYNTHESIS;

EID: 84856330144     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4434-4     Document Type: Article
Times cited : (35)

References (32)
  • 2
    • 0033579483 scopus 로고    scopus 로고
    • Plant cyclotides: A unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif
    • DOI 10.1006/jmbi.1999.3383
    • Craik DJ, Daly NL, Bond T, Waine C. Plant cyclotides: A unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif. J Mol Biol, 1999, 294: 1327-1336 (Pubitemid 30008803)
    • (1999) Journal of Molecular Biology , vol.294 , Issue.5 , pp. 1327-1336
    • Craik, D.J.1    Daly, N.L.2    Bond, T.3    Waine, C.4
  • 3
    • 79958826757 scopus 로고    scopus 로고
    • The chemistry of cyclotides
    • 10.1021/jo200520v 1:CAS:528:DC%2BC3MXmtlWrsbk%3D
    • Craik DJ, Conibear AC. The chemistry of cyclotides. J Org Chem, 2011, 76: 4805-4817
    • (2011) J Org Chem , vol.76 , pp. 4805-4817
    • Craik, D.J.1    Conibear, A.C.2
  • 5
    • 9144274988 scopus 로고    scopus 로고
    • Cyclization of pyrrhocoricin retains structural elements crucial for the antimicrobial activity of the native peptide
    • DOI 10.1002/bip.20159
    • Rosengren KJ, Goransson U, Otvos L, Craik D. Cyclization of pyrrhocoricin retains structural elements crucial for the antimicrobial activity of the native peptide. Biopolymers, 2004, 76: 446-458 (Pubitemid 39540537)
    • (2004) Biopolymers - Peptide Science Section , vol.76 , Issue.5 , pp. 446-458
    • Rosengren, K.J.1    Goransson, U.2    Otvos Jr., L.3    Craik, D.J.4
  • 8
    • 77953454570 scopus 로고    scopus 로고
    • Design and therapeutic applications of cyclotides
    • 10.4155/fmc.09.129 1:CAS:528:DC%2BC3cXmtVejtQ%3D%3D
    • Daly NL, Craik DJ. Design and therapeutic applications of cyclotides. Future Med Chem, 2009, 1: 1613-1622
    • (2009) Future Med Chem , vol.1 , pp. 1613-1622
    • Daly, N.L.1    Craik, D.J.2
  • 9
    • 79958012153 scopus 로고    scopus 로고
    • Bioactive cystine knot proteins
    • 10.1016/j.cbpa.2011.02.008
    • Craik DJ, Daly NL. Bioactive cystine knot proteins. Cur Opin Chem Biol, 2011, 15: 362-368
    • (2011) Cur Opin Chem Biol , vol.15 , pp. 362-368
    • Craik, D.J.1    Daly, N.L.2
  • 10
    • 0030808964 scopus 로고    scopus 로고
    • Synthesis of large cyclic cystine-knot peptide by orthogonal coupling strategy using unprotected peptide precursor
    • DOI 10.1016/S0040-4039(97)01271-9, PII S0040403997012719
    • Tam JP, Lu YA. Synthesis of large cyclic cystine-knot peptide by orthogonal coupling strategy using unprotected peptide precursor. Tetrahedron Lett, 1997, 38: 5599-5602 (Pubitemid 27321132)
    • (1997) Tetrahedron Letters , vol.38 , Issue.32 , pp. 5599-5602
    • Tam, J.P.1    Lu, Y.-A.2
  • 11
    • 0033549108 scopus 로고    scopus 로고
    • Thia zip reaction for synthesis of large cyclic peptides: Mechanisms and applications
    • DOI 10.1021/ja984480u
    • Tam JP, Lu YA, Yu QT. Thia zip reaction for synthesis of large cyclic peptides: Mechanisms and applications. J Am Chem Soc, 1999, 121: 4316-4324 (Pubitemid 29234864)
    • (1999) Journal of the American Chemical Society , vol.121 , Issue.18 , pp. 4316-4324
    • Tam, J.P.1    Lu, Y.-A.2    Yu, Q.3
  • 13
    • 0033543137 scopus 로고    scopus 로고
    • Chemical synthesis and folding pathways of large cyclic polypeptides: Studies of the cystine knot polypeptide kalata B1
    • DOI 10.1021/bi990605b
    • Craik DJ, Daly NL, Love S, Alewood PF. Chemical synthesis and folding pathways of large cyclic polypeptide: Studies of the cystine knot polypeptide kalata B1. Biochemistry, 1999, 38: 10606-10614 (Pubitemid 29383434)
    • (1999) Biochemistry , vol.38 , Issue.32 , pp. 10606-10614
    • Daly, N.L.1    Love, S.2    Alewood, P.F.3    Craik, D.J.4
  • 14
    • 33746467082 scopus 로고    scopus 로고
    • Total synthesis of the macrocyclic cysteine knot microprotein MCoTI-II
    • DOI 10.1039/b607324g
    • Leatherbarrow RJ, Thongyoo P, Tate EW. Total synthesis of the macrocyclic cysteine knot microprotein MCoTI-II. Chem Commun, 2006, 2848-2850 (Pubitemid 44124186)
    • (2006) Chemical Communications , Issue.27 , pp. 2848-2850
    • Thongyoo, P.1    Tate, E.W.2    Leatherbarrow, R.J.3
  • 15
    • 38149104557 scopus 로고    scopus 로고
    • Ultra-stable peptide scaffolds for protein engineering - Synthesis and folding of the circular cystine knotted cyclotide cycloviolacin O2
    • 10.1002/cbic.200700357
    • Goransson U, Aboye TL, Clark RJ, Craik DJ. Ultra-stable peptide scaffolds for protein engineering - Synthesis and folding of the circular cystine knotted cyclotide cycloviolacin O2. ChemBioChem, 2008, 9: 103-113
    • (2008) ChemBioChem , vol.9 , pp. 103-113
    • Goransson, U.1    Aboye, T.L.2    Clark, R.J.3    Craik, D.J.4
  • 16
    • 79951558237 scopus 로고    scopus 로고
    • An Efficient Approach for the total synthesis of cyclotides by microwave assisted Fmoc-SPPS
    • 10.1007/s10989-010-9221-0
    • Goransson U, Park S, Gunasekera S, Aboye TL. An Efficient Approach for the total synthesis of cyclotides by microwave assisted Fmoc-SPPS. Int J Pept Res Ther, 2010, 16: 167-176
    • (2010) Int J Pept Res Ther , vol.16 , pp. 167-176
    • Goransson, U.1    Park, S.2    Gunasekera, S.3    Aboye, T.L.4
  • 17
    • 1542468131 scopus 로고    scopus 로고
    • Chemoselective backbone cyclization of unprotected peptides
    • Camarero JA, Muir TW. Chemoselective backbone cyclization of unprotected peptides. Chem Commun, 1997, 1369-1370 (Pubitemid 127496034)
    • (1997) Chemical Communications , Issue.15 , pp. 1369-1370
    • Camarero, J.A.1    Muir, T.W.2
  • 19
    • 0001176887 scopus 로고    scopus 로고
    • Activation method to prepare a highly reactive acylsulfonamide "safety-catch" linker for solid-phase synthesis
    • 10.1021/ja9535165 1:CAS:528:DyaK28XhsVGgt78%3D
    • Backes BJ, Virgilio AA, Ellman JA. Activation method to prepare a highly reactive acylsulfonamide "safety-catch" linker for solid-phase synthesis. J Am Chem Soc, 1996, 118: 3055-3056
    • (1996) J Am Chem Soc , vol.118 , pp. 3055-3056
    • Backes, B.J.1    Virgilio, A.A.2    Ellman, J.A.3
  • 20
    • 0033572729 scopus 로고    scopus 로고
    • Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry
    • DOI 10.1021/ja992668n
    • Ingenito R, Bianchi E, Fattori D, Pessi A. Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry. J Am Chem Soc, 1999, 121: 11369-11374 (Pubitemid 30010467)
    • (1999) Journal of the American Chemical Society , vol.121 , Issue.49 , pp. 11369-11374
    • Ingenito, R.1    Bianchi, E.2    Fattori, D.3    Pessi, A.4
  • 21
    • 77951100124 scopus 로고    scopus 로고
    • Peptide and protein thioester synthesis via N-to-S acyl transfer
    • 10.1039/b925075a
    • Macmillan D, Kang J. Peptide and protein thioester synthesis via N-to-S acyl transfer. Org Biomol Chem, 2010, 8: 1993-2002
    • (2010) Org Biomol Chem , vol.8 , pp. 1993-2002
    • MacMillan, D.1    Kang, J.2
  • 22
    • 12344274321 scopus 로고    scopus 로고
    • Native chemical ligation through in situ O to S acyl shift
    • DOI 10.1021/ol0481028
    • Botti P, Manganiello S, Gaertner H. Native chemical ligation through in situ O to S acyl shift. Org Lett, 2004, 6: 4861-4864 (Pubitemid 40125828)
    • (2004) Organic Letters , vol.6 , Issue.26 , pp. 4861-4864
    • Botti, P.1    Villain, M.2    Manganiello, S.3    Gaertner, H.4
  • 23
    • 2542548800 scopus 로고    scopus 로고
    • Toward fully synthetic glycoproteins by ultimately convergent routes: A solution to a long-standing problem
    • DOI 10.1021/ja0491836
    • Warren JD, Miller JS, Keding SJ, Danishefsky SJ. Toward fully synthetic glycoproteins by ultimately convergent routes: A solution to a long-standing problem. J Am Chem Soc, 2004, 126: 6576-6578 (Pubitemid 38697358)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.21 , pp. 6576-6578
    • Warren, J.D.1    Miller, J.S.2    Keding, S.J.3    Danishefsky, S.J.4
  • 24
    • 77149155649 scopus 로고    scopus 로고
    • Chemical protein synthesis by kinetically controlled ligation of peptide O-esters
    • 1:CAS:528:DC%2BC3cXis1ehtLY%3D
    • Zheng JS, Cui HK, Fang GM, Xi WX, Liu L. Chemical protein synthesis by kinetically controlled ligation of peptide O-esters. Chem-BioChem, 2010, 11: 511-515
    • (2010) Chem-BioChem , vol.11 , pp. 511-515
    • Zheng, J.S.1    Cui, H.K.2    Fang, G.M.3    Xi, W.X.4    Liu, L.5
  • 25
    • 79955472638 scopus 로고    scopus 로고
    • Fmoc-SPPS chemistry compatible approach for the generation of (glyco)peptide aryl thioesters
    • 10.1016/j.tetlet.2011.03.064 1:CAS:528:DC%2BC3MXltFKju74%3D
    • Zheng JS, Xi WX, Wang FL, Guo QX, Li J. Fmoc-SPPS chemistry compatible approach for the generation of (glyco)peptide aryl thioesters. Tetrahedron Lett, 2011, 52: 2655-2660
    • (2011) Tetrahedron Lett , vol.52 , pp. 2655-2660
    • Zheng, J.S.1    Xi, W.X.2    Wang, F.L.3    Guo, Q.X.4    Li, J.5
  • 26
    • 79960594926 scopus 로고    scopus 로고
    • Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation
    • 10.1021/ja204088a 1:CAS:528:DC%2BC3MXosVCksbc%3D
    • Zheng JS, Chang HN, Wang FL, Liu L. Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation. J Am Chem Soc, 2011, 133: 11080-11083
    • (2011) J Am Chem Soc , vol.133 , pp. 11080-11083
    • Zheng, J.S.1    Chang, H.N.2    Wang, F.L.3    Liu, L.4
  • 28
    • 33646728877 scopus 로고    scopus 로고
    • Insights into the mechanism and catalysis of the native chemical ligation reaction
    • 10.1021/ja058344i 1:CAS:528:DC%2BD28XjvFyitrc%3D
    • Johnson ECB, Kent SBH. Insights into the mechanism and catalysis of the native chemical ligation reaction. J Am Chem Soc, 2006, 128: 6640-6646
    • (2006) J Am Chem Soc , vol.128 , pp. 6640-6646
    • Johnson, E.C.B.1    Kent, S.B.H.2
  • 29
    • 77956283983 scopus 로고    scopus 로고
    • Native chemical ligation applied to the synthesis and bioengineering of circular peptides and proteins
    • 10.1002/bip.21372 1:CAS:528:DC%2BC3cXosF2ht78%3D
    • Clark RJ, Craik D J. Native chemical ligation applied to the synthesis and bioengineering of circular peptides and proteins. Biopolymers, 2010, 94: 414-422
    • (2010) Biopolymers , vol.94 , pp. 414-422
    • Clark, R.J.1    Craik, D.J.2
  • 30
    • 79954580823 scopus 로고    scopus 로고
    • Analysis and classification of circular proteins in CyBase
    • 10.1002/bip.21509
    • Craik DJ, Kaas Q. Analysis and classification of circular proteins in CyBase. Biopolymers, 2010, 94: 584-591
    • (2010) Biopolymers , vol.94 , pp. 584-591
    • Craik, D.J.1    Kaas, Q.2
  • 31
    • 79951662569 scopus 로고    scopus 로고
    • Hydrazine-sensitive thiol protecting group for peptide and protein chemistry
    • 10.1021/ol1028755 1:CAS:528:DC%2BC3MXlt1Oluw%3D%3D
    • Shen F, Zhang ZP, Li JB, Lin Y, Liu L. Hydrazine-sensitive thiol protecting group for peptide and protein chemistry. Org Lett, 2011, 13: 568-571
    • (2011) Org Lett , vol.13 , pp. 568-571
    • Shen, F.1    Zhang, Z.P.2    Li, J.B.3    Lin, Y.4    Liu, L.5


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