메뉴 건너뛰기




Volumn 16, Issue 3, 2010, Pages 191-198

Expanding the scope of native chemical ligation in glycopeptide synthesis

Author keywords

Glycopepide; Glycoprotein; Native chemical ligation; Sialyl TN

Indexed keywords

ALANINE; CYANOGEN BROMIDE; FORMIC ACID; GLYCOPEPTIDE; LYSINE; PHENYLALANINE; S METHYLCYSTEINE; SERINE; SIALOGLYCOPROTEIN; SULFOXIDE; THREONINE; VALINE;

EID: 79951554425     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-010-9226-8     Document Type: Conference Paper
Times cited : (6)

References (39)
  • 1
    • 33746190644 scopus 로고    scopus 로고
    • Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids
    • DOI 10.1002/anie.200503991
    • Bode JW, Fox RM, Baucom KD (2006) Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and a-keto acids. Angew Chem Int Ed 45:1248-1252 (Pubitemid 44097650)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.8 , pp. 1248-1252
    • Bode, J.W.1    Fox, R.M.2    Baucom, K.D.3
  • 2
    • 33845194782 scopus 로고    scopus 로고
    • Sugar-assisted ligation of N-linked glycopeptides with broad sequence tolerance at the ligation junction
    • DOI 10.1021/ja065601q
    • Brik A, Ficht S, Yang YY, Bennett CS, Wong CH (2006) Sugar-assisted ligation of N-linked glycopeptides with broad sequence tolerance at the ligation junction. J Am Chem Soc 128:15026-15033 (Pubitemid 44851643)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.46 , pp. 15026-15033
    • Brik, A.1    Ficht, S.2    Yang, Y.-Y.3    Bennett, C.S.4    Wong, C.-H.5
  • 3
    • 54249149331 scopus 로고    scopus 로고
    • Native chemical ligation at valine: A contribution to peptide and glycopeptide synthesis
    • Chen J, Wan Q, Yuan Y, Zhu JL, Danishefsky SJ (2008) Native chemical ligation at valine: a contribution to peptide and glycopeptide synthesis. Angew Chem Int Ed 47:8521-8524
    • (2008) Angew Chem Int Ed , vol.47 , pp. 8521-8524
    • Chen, J.1    Wan, Q.2    Yuan, Y.3    Zhu, J.L.4    Danishefsky, S.J.5
  • 4
    • 77649190705 scopus 로고    scopus 로고
    • A program for ligation at threonine sites: Application to the controlled total synthesis of glycopeptides
    • Chen J, Wang P, Zhu JL, Wan Q, Danishefsky SJ (2010) A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides. Tetrahedron 66:2277-2283
    • (2010) Tetrahedron , vol.66 , pp. 2277-2283
    • Chen, J.1    Wang, P.2    Zhu, J.L.3    Wan, Q.4    Danishefsky, S.J.5
  • 6
    • 0027944205 scopus 로고
    • Synthesis of proteins by native chemical ligation
    • Dawson PE, Muir TW, Clark-Lewis I, Kent SBH (1994) Synthesis of proteins by native chemical ligation. Science 266:776-779 (Pubitemid 24359280)
    • (1994) Science , vol.266 , Issue.5186 , pp. 776-779
    • Dawson, P.E.1    Muir, T.W.2    Clark-Lewis, I.3    Kent, S.B.H.4
  • 7
    • 57549083785 scopus 로고    scopus 로고
    • Expanding the scope of chemoselective peptide ligation in chemical biology
    • Dirksen A, Dawson PE (2008) Expanding the scope of chemoselective peptide ligation in chemical biology. Curr Opin Chem Biol 12:760-766
    • (2008) Curr Opin Chem Biol , vol.12 , pp. 760-766
    • Dirksen, A.1    Dawson, P.E.2
  • 8
    • 20844437106 scopus 로고    scopus 로고
    • Glycans in cancer and inflammation - Potential for therapeutics and diagnostics
    • DOI 10.1038/nrd1751
    • Dube DH, Bertozzi CR (2005) Glycans in cancer and inflammation. Potential for therapeutics and diagnostics. Nat Rev Drug Discov 4:477-488 (Pubitemid 40861990)
    • (2005) Nature Reviews Drug Discovery , vol.4 , Issue.6 , pp. 477-488
    • Dube, D.H.1    Bertozzi, C.R.2
  • 10
    • 0001094662 scopus 로고    scopus 로고
    • Glycobiology: Toward understanding the function of sugars
    • Dwek RA (1996) Glycobiology: toward understanding the function of sugars. Chem Rev 96:683-720 (Pubitemid 126649163)
    • (1996) Chemical Reviews , vol.96 , Issue.2 , pp. 683-720
    • Dwek, R.A.1
  • 12
    • 0016149597 scopus 로고
    • Reaction of cyanogen-bromide with S-methylcysteine - Fragmentation of peptide 14-29 of bovine pancreatic ribonuclease-A
    • Gross E, Morell JL (1974) Reaction of cyanogen-bromide with S-methylcysteine - fragmentation of peptide 14-29 of bovine pancreatic ribonuclease-A. Biochem Biophys Res Commun 59:1145-1150
    • (1974) Biochem Biophys Res Commun , vol.59 , pp. 1145-1150
    • Gross, E.1    Morell, J.L.2
  • 13
    • 52449084906 scopus 로고    scopus 로고
    • Native chemical ligation at valine
    • Haase C, Rohde H, Seitz O (2008) Native chemical ligation at valine. Angew Chem Int Ed 47:6807-6810
    • (2008) Angew Chem Int Ed , vol.47 , pp. 6807-6810
    • Haase, C.1    Rohde, H.2    Seitz, O.3
  • 15
    • 57749121492 scopus 로고    scopus 로고
    • Chemoselective ligation and modification strategies for peptides and proteins
    • Hackenberger CPR, Schwarzer D (2008) Chemoselective ligation and modification strategies for peptides and proteins. Angew Chem Int Ed 47:10030-10074
    • (2008) Angew Chem Int Ed , vol.47 , pp. 10030-10074
    • Hackenberger, C.P.R.1    Schwarzer, D.2
  • 16
    • 73249150910 scopus 로고    scopus 로고
    • Design and synthesis of a homogeneous erythropoietin analogue having two human complex type sialyloligosaccharides by combined use of chemical and bacterial protein expression methods
    • Hirano K, Macmillan D, Tezuka K, Tsuji T, Kajihara Y (2009) Design and synthesis of a homogeneous erythropoietin analogue having two human complex type sialyloligosaccharides by combined use of chemical and bacterial protein expression methods. Angew Chem Int Ed 48:9557-9560
    • (2009) Angew Chem Int Ed , vol.48 , pp. 9557-9560
    • Hirano, K.1    MacMillan, D.2    Tezuka, K.3    Tsuji, T.4    Kajihara, Y.5
  • 17
    • 34247473463 scopus 로고    scopus 로고
    • Recent progress in the field of glycopeptide synthesis
    • DOI 10.1002/bip.20699
    • Hojo H, Nakahara Y (2007) Recent progress in the field of glycopeptide synthesis. Biopolymers 88:308-324 (Pubitemid 46657996)
    • (2007) Biopolymers - Peptide Science Section , vol.88 , Issue.2 , pp. 308-324
    • Hojo, H.1    Nakahara, Y.2
  • 18
    • 33646728877 scopus 로고    scopus 로고
    • Insights into the mechanism and catalysis of the native chemical ligation reaction
    • Johnson ECB, Kent SBH (2006) Insights into the mechanism and catalysis of the native chemical ligation reaction. J Am Chem Soc 128:6640-6646
    • (2006) J Am Chem Soc , vol.128 , pp. 6640-6646
    • Johnson, E.C.B.1    Kent, S.B.H.2
  • 19
    • 0032953154 scopus 로고    scopus 로고
    • Enhancement of cyanogen bromide cleavage yields for methionyl-serine and methionyl-threonine peptide bonds
    • DOI 10.1006/abio.1998.2945
    • Kaiser R, Metzka L (1999) Enhancement of cyanogen bromide cleavage yields for methionyl-serine and methionyl-threonine peptide bonds. Anal Biochem 266:1-8 (Pubitemid 29024602)
    • (1999) Analytical Biochemistry , vol.266 , Issue.1 , pp. 1-8
    • Kaiser, R.1    Metzka, L.2
  • 20
    • 33646910318 scopus 로고    scopus 로고
    • Convenient synthesis of a sialylglycopeptide-thioester having an intact and homogeneous complex-type disialyl-oligosaccharide
    • DOI 10.1016/j.carres.2006.04.037, PII S0008621506002072
    • Kajihara Y, Yoshihara A, Hirano K, Yamamoto N (2006) Convenient synthesis of a sialylglycopeptide-thioester having an intact and homogeneous complex-type disialyl-oligosaccharide. Carbohydr Res 341:1333-1340 (Pubitemid 43795409)
    • (2006) Carbohydrate Research , vol.341 , Issue.10 , pp. 1333-1340
    • Kajihara, Y.1    Yoshihara, A.2    Hirano, K.3    Yamamoto, N.4
  • 22
    • 62449282062 scopus 로고    scopus 로고
    • Total chemical synthesis of proteins
    • Kent SBH (2009) Total chemical synthesis of proteins. Chem Soc Rev 38:338-351
    • (2009) Chem Soc Rev , vol.38 , pp. 338-351
    • Kent, S.B.H.1
  • 23
    • 0034729576 scopus 로고    scopus 로고
    • Staudinger ligation: A peptide from a thioester and azide
    • Nilsson BL, Kiessling LL, Raines RT (2000) Staudinger ligation: a peptide from a thioester and azide. Org Lett 2:1939-1941
    • (2000) Org Lett , vol.2 , pp. 1939-1941
    • Nilsson, B.L.1    Kiessling, L.L.2    Raines, R.T.3
  • 24
    • 0035843279 scopus 로고    scopus 로고
    • High-yielding staudinger ligation of a phosphinothioester and azide to form a peptide
    • DOI 10.1021/ol006739v
    • Nilsson BL, Kiessling LL, Raines RT (2001) High-yielding Staudinger ligation of a phosphinothioester and azide to form a peptide. Org Lett 3:9-12 (Pubitemid 33621078)
    • (2001) Organic Letters , vol.3 , Issue.1 , pp. 9-12
    • Nilsson, B.L.1    Kiessling, L.L.2    Raines, R.T.3
  • 26
    • 49149087660 scopus 로고    scopus 로고
    • Uncovering a latent ligation site for glycopeptide synthesis
    • Okamoto R, Kajihara Y (2008) Uncovering a latent ligation site for glycopeptide synthesis. Angew Chem Int Ed 47:5402-5406
    • (2008) Angew Chem Int Ed , vol.47 , pp. 5402-5406
    • Okamoto, R.1    Kajihara, Y.2
  • 28
    • 0037267249 scopus 로고    scopus 로고
    • Synthesis of methionine containing peptides related to native chemical ligation
    • Pachamuthu K, Schmidt RR (2003) Synthesis of methionine containing peptides related to native chemical ligation. Synlett 659-662 (Pubitemid 36469585)
    • (2003) Synlett , Issue.5 , pp. 659-662
    • Pachamuthu, K.1    Schmidt, R.R.2
  • 29
    • 72149096309 scopus 로고    scopus 로고
    • Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins
    • Payne RJ, Wong CH (2010) Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins. Chem Commun 46:21-43
    • (2010) Chem Commun , vol.46 , pp. 21-43
    • Payne, R.J.1    Wong, C.H.2
  • 30
    • 46749125397 scopus 로고    scopus 로고
    • Cysteine-free peptide and glycopeptide ligation by direct aminolysis
    • Payne RJ, Ficht S, Greenberg WA, Wong CH (2008) Cysteine-free peptide and glycopeptide ligation by direct aminolysis. Angew Chem Int Ed 47:4411-4415
    • (2008) Angew Chem Int Ed , vol.47 , pp. 4411-4415
    • Payne, R.J.1    Ficht, S.2    Greenberg, W.A.3    Wong, C.H.4
  • 31
    • 58149198802 scopus 로고    scopus 로고
    • Optimisation of chemical protein cleavage for erythropoietin semi-synthesis using native chemical ligation
    • Richardson JP, Macmillan D (2008) Optimisation of chemical protein cleavage for erythropoietin semi-synthesis using native chemical ligation. Org Biomol Chem 6:3977-3982
    • (2008) Org Biomol Chem , vol.6 , pp. 3977-3982
    • Richardson, J.P.1    MacMillan, D.2
  • 32
    • 0034643993 scopus 로고    scopus 로고
    • A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds
    • Saxon E, Armstrong JI, Bertozzi CR (2000) A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds. Org Lett 2:2141-2143
    • (2000) Org Lett , vol.2 , pp. 2141-2143
    • Saxon, E.1    Armstrong, J.I.2    Bertozzi, C.R.3
  • 33
    • 34548214630 scopus 로고    scopus 로고
    • A target molecule for cancer therapy
    • Singh R, Bandyopadhyay D (2007) MUC1-a target molecule for cancer therapy. Cancer Biol Ther 6:481-486 (Pubitemid 47328319)
    • (2007) Cancer Biology and Therapy , vol.6 , Issue.4 , pp. 481-486
    • Singh, R.1    Bandyopadhyay, D.2
  • 34
    • 67449119292 scopus 로고    scopus 로고
    • Effects of glycosylation on the stability of protein pharmaceuticals
    • Sola RJ, Griebenow K (2009) Effects of glycosylation on the stability of protein pharmaceuticals. J Pharm Sci 98:1223-1245
    • (2009) J Pharm Sci , vol.98 , pp. 1223-1245
    • Sola, R.J.1    Griebenow, K.2
  • 35
    • 0032189519 scopus 로고    scopus 로고
    • Methionine ligation strategy in the biomimetic synthesis of parathyroid hormones
    • Tam JP, Yu Q (1998) Methionine ligation strategy in the biomimetic synthesis of parathyroid hormones. Biopolymers 46:319-327
    • (1998) Biopolymers , vol.46 , pp. 319-327
    • Tam, J.P.1    Yu, Q.2
  • 36
    • 33749860977 scopus 로고    scopus 로고
    • Post-translational modifications in the context of therapeutic proteins
    • DOI 10.1038/nbt1252, PII NBT1252
    • Walsh G, Jefferis R (2006) Post-translational modifications in the context of therapeutic proteins. Nat Biotechnol 24:1241-1252 (Pubitemid 44564769)
    • (2006) Nature Biotechnology , vol.24 , Issue.10 , pp. 1241-1252
    • Walsh, G.1    Jefferis, R.2
  • 37
    • 37349094422 scopus 로고    scopus 로고
    • Free-radical-based, specific desulfurization of cysteine: A powerful advance in the synthesis of polypeptides and glycopolypeptides
    • DOI 10.1002/anie.200704195
    • Wan Q, Danishefsky SJ (2007) Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides. Angew Chem Int Ed 46:9248-9252 (Pubitemid 350292152)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.48 , pp. 9248-9252
    • Wan, Q.1    Danishefsky, S.J.2
  • 38
    • 0035977638 scopus 로고    scopus 로고
    • Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization
    • DOI 10.1021/ja003265m
    • Yan LZ, Dawson PE (2001) Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization. J Am Chem Soc 123:526-533 (Pubitemid 32105995)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.4 , pp. 526-533
    • Yan, L.Z.1    Dawson, P.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.