SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 12, Issue 29, 2014, Pages 5536-5543

Solid phase oxime ligations for the iterative synthesis of polypeptide conjugates

(4) Decostaire, Isidore E a Lelièvre, Dominique a Aucagne, Vincent a Delmas, Agnès F a

a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; MATERIALS HANDLING; PEPTIDES; POLYPEPTIDES;

BIOMACROMOLECULES; CHEMICAL TRANSFORMATIONS; CHEMOSELECTIVE COUPLING; CHROMATOGRAPHIC PURIFICATION; ITERATIVE SYNTHESIS; LIGATION REACTIONS; NATIVE CHEMICAL LIGATION; OPTIMAL CONDITIONS;

SURGICAL EQUIPMENT;

ALDEHYDE; MUCIN 1; OXIME; PEPTIDE; WATER;

AMINO ACID SEQUENCE; CHEMISTRY; MOLECULAR GENETICS; PROCEDURES; SOLID PHASE SYNTHESIS; SYNTHESIS;

ALDEHYDES; AMINO ACID SEQUENCE; MOLECULAR SEQUENCE DATA; MUCIN-1; OXIMES; PEPTIDES; SOLID-PHASE SYNTHESIS TECHNIQUES; WATER;

EID: 84903756603 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c4ob00760c Document Type: Article

Times cited : (20)

References (52)

1
- 20744456789
- R. B. Merrifield J. Am. Chem. Soc. 1963 85 2149 2154
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
- Merrifield, R.B.¹

2
- 0022699646
- R. B. Merrifield Science 1986 232 341 347
- (1986) Science , vol.232 , pp. 341-347
- Merrifield, R.B.¹

3
- 0033615313
- L. E. Canne P. Botti R. J. Simon Y. Chen E. A. Dennis S. B. H. Kent J. Am. Chem. Soc. 1999 121 8720 8727
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 8720-8727
- Canne, L.E.¹ Botti, P.² Simon, R.J.³ Chen, Y.⁴ Dennis, E.A.⁵ Kent, S.B.H.⁶

4
- 0034674698
- A. Brik E. Keinan P. E. Dawson J. Org. Chem. 2000 65 3829 3835
- (2000) J. Org. Chem. , vol.65 , pp. 3829-3835
- Brik, A.¹ Keinan, E.² Dawson, P.E.³

5
- 0034177596
- G. J. Cotton T. W. Muir Chem. Biol. 2000 7 253 261
- (2000) Chem. Biol. , vol.7 , pp. 253-261
- Cotton, G.J.¹ Muir, T.W.²

6
- 33744505598
- E. C. Johnson T. Durek S. B. Kent Angew. Chem., Int. Ed. 2006 45 3283 3287
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3283-3287
- Johnson, E.C.¹ Durek, T.² Kent, S.B.³

7
- 84903789001
- L. Raibaut H. Adihou R. Desmet A. F. Delmas V. Aucagne O. Melnyk Chem. Sci. 2013 4 3839 3844
- (2013) Chem. Sci. , vol.4 , pp. 3839-3844
- Raibaut, L.¹ Adihou, H.² Desmet, R.³ Delmas, A.F.⁴ Aucagne, V.⁵ Melnyk, O.⁶

8
- 84880346917
- T. Wang S. J. Danishefsky Proc. Natl. Acad. Sci. U. S. A. 2013 110 11708 11713
- (2013) Proc. Natl. Acad. Sci. U. S. A. , vol.110 , pp. 11708-11713
- Wang, T.¹ Danishefsky, S.J.²

9
- 84868154433
- (see also references therein for the self-purification effect)
- V. Aucagne I. E. Valverde P. Marceau M. Galibert N. Dendane A. F. Delmas Angew. Chem., Int. Ed. 2012 51 11320 11324
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 11320-11324
- Aucagne, V.¹ Valverde, I.E.² Marceau, P.³ Galibert, M.⁴ Dendane, N.⁵ Delmas, A.F.⁶

10
- 84882248564
- J. Qiu A. H. El-Sagheer T. Brown Chem. Commun. 2013 49 6959 6961
- (2013) Chem. Commun. , vol.49 , pp. 6959-6961
- Qiu, J.¹ El-Sagheer, A.H.² Brown, T.³

11
- 84866416513
- L. Raibaut N. Ollivier O. Melnyk Chem. Soc. Rev. 2012 41 7001 7015
- (2012) Chem. Soc. Rev. , vol.41 , pp. 7001-7015
- Raibaut, L.¹ Ollivier, N.² Melnyk, O.³

12
- 84879150415
- Whereas SPPS implies the use of side chain protected amino acids as building blocks for the iterative process, SPCL uses naked peptides as building blocks
- D. Verzele A. Madder ChemBioChem 2013 14 1032 1048
- (2013) ChemBioChem , vol.14 , pp. 1032-1048
- Verzele, D.¹ Madder, A.²

13
- 84891490365
- S. Ulrich D. Boturyn A. Marra O. Renaudet P. Dumy Chem.-Eur. J. 2014 20 34 41
- (2014) Chem.-Eur. J. , vol.20 , pp. 34-41
- Ulrich, S.¹ Boturyn, D.² Marra, A.³ Renaudet, O.⁴ Dumy, P.⁵

14
- 0028231302
- K. Rose J. Am. Chem. Soc. 1994 116 30 33
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 30-33
- Rose, K.¹

15
- 0028960723
- Some definitions of "linker": an immobilized protecting group
- J. Shao J. P. Tam J. Am. Chem. Soc. 1995 117 3893 3899
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3893-3899
- Shao, J.¹ Tam, J.P.²

16
- 0033683359
- a specialized protecting group that attaches the peptide to the support
- F. Guillier D. Orain M. Bradley Chem. Rev. 2000 100 2091 2157
- (2000) Chem. Rev. , vol.100 , pp. 2091-2157
- Guillier, F.¹ Orain, D.² Bradley, M.³

17
- 84877768915
- M. Góngora-Benítez J. Tulla-Puche F. Albericio ACS Comb. Sci. 2013 15 217 228
- (2013) ACS Comb. Sci. , vol.15 , pp. 217-228
- Góngora-Benítez, M.¹ Tulla-Puche, J.² Albericio, F.³

18
- 0023741252
- See for example
- S. Gendler J. Taylor-Papadimitriou T. Duhig J. Rothbard J. Burchell J. Biol. Chem. 1988 263 12820 12823
- (1988) J. Biol. Chem. , vol.263 , pp. 12820-12823
- Gendler, S.¹ Taylor-Papadimitriou, J.² Duhig, T.³ Rothbard, J.⁴ Burchell, J.⁵

19
- 84882978971
- D. Al Sheikha B. L. Wilkinson G. Santhakumar M. Thaysen-Andersen R. J. Payne Org. Biomol. Chem. 2013 11 6090 6096
- (2013) Org. Biomol. Chem. , vol.11 , pp. 6090-6096
- Al Sheikha, D.¹ Wilkinson, B.L.² Santhakumar, G.³ Thaysen-Andersen, M.⁴ Payne, R.J.⁵

20
- 84881164473
- A. Novoa S. Barluenga C. Serba N. Winssinger Chem. Commun. 2013 49 7608 7610
- (2013) Chem. Commun. , vol.49 , pp. 7608-7610
- Novoa, A.¹ Barluenga, S.² Serba, C.³ Winssinger, N.⁴

21
- 84879482621
- C. Xu H. Y. Lam Y. Zhang X. Li Chem. Commun. 2013 49 6200 6202
- (2013) Chem. Commun. , vol.49 , pp. 6200-6202
- Xu, C.¹ Lam, H.Y.² Zhang, Y.³ Li, X.⁴

22
- 49149087660
- See for example
- R. Okamoto Y. Kajihara Angew. Chem., Int. Ed. 2008 47 5402 5406
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 5402-5406
- Okamoto, R.¹ Kajihara, Y.²

23
- 33749028981
- G. A. Cremer N. Bureaud V. Piller H. Kunz F. Piller A. F. Delmas ChemMedChem 2006 1 965 968
- (2006) ChemMedChem , vol.1 , pp. 965-968
- Cremer, G.A.¹ Bureaud, N.² Piller, V.³ Kunz, H.⁴ Piller, F.⁵ Delmas, A.F.⁶

24
- 84876898171
- N. Gaidzik U. Westerlind H. Kunz Chem. Soc. Rev. 2013 42 4421 4442
- (2013) Chem. Soc. Rev. , vol.42 , pp. 4421-4442
- Gaidzik, N.¹ Westerlind, U.² Kunz, H.³

25
- 34548660856
- S. Ingale M. A. Wolfert J. Gaekwad T. Buskas G. J. Boons Nat. Chem. Biol. 2007 3 663 667
- (2007) Nat. Chem. Biol. , vol.3 , pp. 663-667
- Ingale, S.¹ Wolfert, M.A.² Gaekwad, J.³ Buskas, T.⁴ Boons, G.J.⁵

26
- 34548593215
- C. Napoletano A. Rughetti M. P. Agervig Tarp J. Coleman E. P. Bennett G. Picco P. Sale K. Denda-Nagai T. Irimura U. Mandel H. Clausen L. Frati J. Taylor-Papadimitriou J. Burchell M. Nuti Cancer Res. 2007 67 8358 8367
- (2007) Cancer Res. , vol.67 , pp. 8358-8367
- Napoletano, C.¹ Rughetti, A.² Agervig Tarp, M.P.³ Coleman, J.⁴ Bennett, E.P.⁵ Picco, G.⁶ Sale, P.⁷ Denda-Nagai, K.⁸ Irimura, T.⁹ Mandel, U.¹⁰ Clausen, H.¹¹ Frati, L.¹² Taylor-Papadimitriou, J.¹³ Burchell, J.¹⁴ Nuti, M.¹⁵

27
- 79851470018
- B. L. Wilkinson S. Day L. R. Malins V. Apostolopoulos R. J. Payne Angew. Chem., Int. Ed. 2011 50 1635 1639
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 1635-1639
- Wilkinson, B.L.¹ Day, S.² Malins, L.R.³ Apostolopoulos, V.⁴ Payne, R.J.⁵

28
- 54749084565
- J. Kalia R. T. Raines Angew. Chem., Int. Ed. 2008 47 7523 7526
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7523-7526
- Kalia, J.¹ Raines, R.T.²

29
- 0035168781
- E. H. Nardin J. M. Calvo-Calle G. A. Oliveira R. S. Nussenzweig M. Schneider J. M. Tiercy L. Loutan D. Hochstrasser K. Rose J. Immunol. 2001 166 481 489
- (2001) J. Immunol. , vol.166 , pp. 481-489
- Nardin, E.H.¹ Calvo-Calle, J.M.² Oliveira, G.A.³ Nussenzweig, R.S.⁴ Schneider, M.⁵ Tiercy, J.M.⁶ Loutan, L.⁷ Hochstrasser, D.⁸ Rose, K.⁹

30
- 47649099501
- O. Renaudet L. BenMohamed G. Dasgupta I. Bettahi P. Dumy ChemMedChem 2008 3 737 741
- (2008) ChemMedChem , vol.3 , pp. 737-741
- Renaudet, O.¹ Benmohamed, L.² Dasgupta, G.³ Bettahi, I.⁴ Dumy, P.⁵

31
- 84862529920
- W. Zeng K. Azzopardi D. Hocking C. Y. Wong G. Robevska M. Tauschek R. M. Robins-Browne D. C. Jackson Vaccine 2012 30 4800 4806
- (2012) Vaccine , vol.30 , pp. 4800-4806
- Zeng, W.¹ Azzopardi, K.² Hocking, D.³ Wong, C.Y.⁴ Robevska, G.⁵ Tauschek, M.⁶ Robins-Browne, R.M.⁷ Jackson, D.C.⁸

32
- 0033990731
- W. Zeng D. C. Jackson J. Murray K. Rose L. E. Brown Vaccine 2000 18 1031 1039
- (2000) Vaccine , vol.18 , pp. 1031-1039
- Zeng, W.¹ Jackson, D.C.² Murray, J.³ Rose, K.⁴ Brown, L.E.⁵

33
- 10944228789
- G. A. Cremer N. Bureaud D. Lelièvre V. Piller F. Piller A. Delmas Chem.-Eur. J. 2004 10 6353 6360
- (2004) Chem.-Eur. J. , vol.10 , pp. 6353-6360
- Cremer, G.A.¹ Bureaud, N.² Lelièvre, D.³ Piller, V.⁴ Piller, F.⁵ Delmas, A.⁶

34
- 13444301106
- For a recent review on chemoselectivity, see
- H. Shao M. M. Crnogorac T. Kong S.-Y. Chen J. M. Williams J. M. Tack V. Gueriguian E. N. Cagle M. Carnevali D. Tumelty X. Paliard L. P. Miranda J. A. Bradburne G. G. Kochendoerfer J. Am. Chem. Soc. 2005 127 1350 1351
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 1350-1351
- Shao, H.¹ Crnogorac, M.M.² Kong, T.³ Chen, S.-Y.⁴ Williams, J.M.⁵ Tack, J.M.⁶ Gueriguian, V.⁷ Cagle, E.N.⁸ Carnevali, M.⁹ Tumelty, D.¹⁰ Paliard, X.¹¹ Miranda, L.P.¹² Bradburne, J.A.¹³ Kochendoerfer, G.G.¹⁴

35
- 84873292926
- C. H. Wong S. C. Zimmerman Chem. Commun. 2013 49 1679 1695
- (2013) Chem. Commun. , vol.49 , pp. 1679-1695
- Wong, C.H.¹ Zimmerman, S.C.²

36
- 0022091975
- F. Albericio G. Barany Int. J. Pept. Protein Res. 1985 26 92 97
- (1985) Int. J. Pept. Protein Res. , vol.26 , pp. 92-97
- Albericio, F.¹ Barany, G.²

37
- 0026024820
- K. Barlos O. Chatzi D. Gatos G. Stavropoulos T. Tsegenidis Tetrahedron Lett. 1991 32 475 478
- (1991) Tetrahedron Lett. , vol.32 , pp. 475-478
- Barlos, K.¹ Chatzi, O.² Gatos, D.³ Stavropoulos, G.⁴ Tsegenidis, T.⁵

38
- 0030590456
- F. Wahl M. Mutter Tetrahedron Lett. 1996 37 6861 6864
- (1996) Tetrahedron Lett. , vol.37 , pp. 6861-6864
- Wahl, F.¹ Mutter, M.²

39
- 0032568384
- F. Guibé Tetrahedron 1998 54 2967 3042
- (1998) Tetrahedron , vol.54 , pp. 2967-3042
- Guibé, F.¹

40
- 0032564556
- D. Lelièvre H. Chabane A. Delmas Tetrahedron Lett. 1998 39 9675 9678
- (1998) Tetrahedron Lett. , vol.39 , pp. 9675-9678
- Lelièvre, D.¹ Chabane, H.² Delmas, A.³

41
- 0036642737
- D. Lelièvre O. Turpin S. El Kassouli A. Delmas Tetrahedron 2002 28 5525 5533
- (2002) Tetrahedron , vol.28 , pp. 5525-5533
- Lelièvre, D.¹ Turpin, O.² El Kassouli, S.³ Delmas, A.⁴

42
- 33747810496
- I. E. Decostaire D. Lelièvre H. Zhang A. F. Delmas Tetrahedron Lett. 2006 47 7057 7060
- (2006) Tetrahedron Lett. , vol.47 , pp. 7057-7060
- Decostaire, I.E.¹ Lelièvre, D.² Zhang, H.³ Delmas, A.F.⁴

43
- 34547874240
- C. Jimenez-Castells B. G. de la Torre R. Gutierrez Gallego D. Andreu Bioorg. Med. Chem. Lett. 2007 17 5155 5158
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 5155-5158
- Jimenez-Castells, C.¹ De La Torre, B.G.² Gutierrez Gallego, R.³ Andreu, D.⁴

44
- 78650246909
- G. Mezo I. Szabo I. Kertesz R. Hegedus E. Orban U. Leurs S. Bosze G. Halmos M. Manea J. Pept. Sci. 2011 17 39 46
- (2011) J. Pept. Sci. , vol.17 , pp. 39-46
- Mezo, G.¹ Szabo, I.² Kertesz, I.³ Hegedus, R.⁴ Orban, E.⁵ Leurs, U.⁶ Bosze, S.⁷ Halmos, G.⁸ Manea, M.⁹

45
- 0027414871
- U. Kertscher M. Bienert E. Krause N. F. Sepeton B. Mehlis Int. J. Pept. Protein Res. 1993 43 207 211
- (1993) Int. J. Pept. Protein Res. , vol.43 , pp. 207-211
- Kertscher, U.¹ Bienert, M.² Krause, E.³ Sepeton, N.F.⁴ Mehlis, B.⁵

46
- 0028022901
- J. E. Battersby W. S. Hancock E. Canova-Davis J. Oeswein B. O'Connor Int. J. Pept. Protein Res. 1994 44 215 222
- (1994) Int. J. Pept. Protein Res. , vol.44 , pp. 215-222
- Battersby, J.E.¹ Hancock, W.S.² Canova-Davis, E.³ Oeswein, J.⁴ O'Connor, B.⁵

47
- 0030657857
- N. Thieriet J. Alsina E. Giralt F. Guibé F. Albericio Tetrahedron Lett. 1997 38 7275 7278
- (1997) Tetrahedron Lett. , vol.38 , pp. 7275-7278
- Thieriet, N.¹ Alsina, J.² Giralt, E.³ Guibé, F.⁴ Albericio, F.⁵

48
- 34547757891
- I. E. Decostaire D. Lelièvre V. Aucagne A. F. Delmas Tetrahedron Lett. 2007 48 6523 6526
- (2007) Tetrahedron Lett. , vol.48 , pp. 6523-6526
- Decostaire, I.E.¹ Lelièvre, D.² Aucagne, V.³ Delmas, A.F.⁴

49
- 0029140496
- L. E. Canne A. R. Ferré-d'Amaré S. K. Burley S. B. H. Kent J. Am. Chem. Soc. 1995 117 2998 3007
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 2998-3007
- Canne, L.E.¹ Ferré-D'Amaré, A.R.² Burley, S.K.³ Kent, S.B.H.⁴

50
- 0030250872
- K. Rose W. Zeng P. O. Regamey I. V. Chernushevich K. G. Standing H. F. Gaertner Bioconjugate Chem. 1996 7 552 556
- (1996) Bioconjugate Chem. , vol.7 , pp. 552-556
- Rose, K.¹ Zeng, W.² Regamey, P.O.³ Chernushevich, I.V.⁴ Standing, K.G.⁵ Gaertner, H.F.⁶

51
- 0033660334
- C. Buré D. Lelièvre A. Delmas Rapid Commun. Mass Spectrom. 2000 14 2158 2164
- (2000) Rapid Commun. Mass Spectrom. , vol.14 , pp. 2158-2164
- Buré, C.¹ Lelièvre, D.² Delmas, A.³

52
- 79959676475
- J. Hardouin G.-A. Cremer A. F. Delmas Rapid Commun. Mass Spectrom. 2011 25 2106 2112
- (2011) Rapid Commun. Mass Spectrom. , vol.25 , pp. 2106-2112
- Hardouin, J.¹ Cremer, G.-A.² Delmas, A.F.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.