SCOPUS 정보 검색 플랫폼

Volumn , Issue 21, 2009, Pages 2999-3001

A general sequence independent solid phase method for the site specific synthesis of multiple sulfated-tyrosine containing peptides

(7) Bunschoten, Anton a Kruijtzer, John A W a Ippel, Johannes H a De Haas, Carla J C b Van Strijp, Jos A G b Kemmink, Johan a Liskamp, Rob M J a

a UTRECHT UNIVERSITY (Netherlands)

b UNIVERSITY MEDICAL CENTER UTRECHT (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; COMPLEMENT COMPONENT C5A RECEPTOR; FLUORENYLMETHYLOXYCARBONYL DERIVATIVE; G PROTEIN COUPLED RECEPTOR; LEUCINE ENKEPHALIN; NEUROPEPTIDE; SULFATE; SYNTHETIC PEPTIDE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PEPTIDE SYNTHESIS; PHYSICAL PHASE; PROTEIN PROTEIN INTERACTION; SOLID; SULFATION;

EID: 65949104067 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b823425f Document Type: Article

Times cited : (21)

References (19)

1
- 46749128220
- C. Seibert T. P. Sakmar Protein Sci. 2008 90 459 477
- (2008) Protein Sci. , vol.90 , pp. 459-477
- Seibert, C.¹ Sakmar, T.P.²

2
- 33947597664
- A. S. Woods H. J. Wang S. N. Jackson J. Proteome Res. 2007 6 1176 1182
- (2007) J. Proteome Res. , vol.6 , pp. 1176-1182
- Woods, A.S.¹ Wang, H.J.² Jackson, S.N.³

3
- 0041589205
- K. L. Moore J. Biol. Chem. 2003 278 24243 24246
- (2003) J. Biol. Chem. , vol.278 , pp. 24243-24246
- Moore, K.L.¹

4
- 0034014055
- J. W. Kehoe C. R. Bertozzi Chem. Biol. 2000 7 R57 R61
- (2000) Chem. Biol. , vol.7
- Kehoe, J.W.¹ Bertozzi, C.R.²

5
- 0019980586
- W. B. Huttner Nature 1982 299 273 276
- (1982) Nature , vol.299 , pp. 273-276
- Huttner, W.B.¹

6
- 65949101523
- Compared to phosphorylated Tyr residues, the O-sulfate linkage is highly acid labile which creates problems during conventional Fmoc-tBu based SPPS, see:
- In addition to Tyr phosphorylation (1.8%), as much as 1% of all Tyr residues of the total protein in an organism can be sulfated making these the two most frequently occurring forms of post-translational modification of this amino acid residue. In contrast to Ser (86%) and Thr (12%) phosphorylation, sulfation of Ser and Thr is quite rare
- Adition to Tyr Phosphorylation (1.8%), As Much As 1% of All Tyr Residues of the Total Protein in An Organism Can Be Sulfated Making These the Two Most Frequently Occurring Forms of Post-translational Modification of This Amino Acid Residue. in Contrast to ser (86%) and Thr (12%) Phosphorylation, Sulfation of ser and Thr Is Quite Rare

7
- 33847418755
- D. Balsved J. R. Bundgaard J. W. Sen Anal. Biochem. 2007 363 70 76
- (2007) Anal. Biochem. , vol.363 , pp. 70-76
- Balsved, D.¹ Bundgaard, J.R.² Sen, J.W.³

8
- 65949107909
- Angew. Chem., Int. Ed. 2002 41 3449 3451
- T. Young L. L. Kiessling Angew. Chem. 2002 114 3599 3451 Angew. Chem., Int. Ed. 2002 41 3449 3451
- (2002) Angew. Chem. , vol.114 , Issue.3599 , pp. 3451
- Young, T.¹ Kiessling, L.L.²

9
- 65949097570
- M. Goodman, A. Felix, L. Moroder and C. Toniolo, Georg Thieme Verlag, Stuttgart and New York, pp. 425-453
- H.-J. Musiol, A. Escherich and L. Moroder, in Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics, ed., M. Goodman, A. Felix, L. Moroder, and, C. Toniolo, Georg Thieme Verlag, Stuttgart and New York, 2003, ch. 6.6, vol. E22b, pp. 425-453
- (2003) Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics, Ed.
- Musiol, H.-J.¹ Escherich, A.² Moroder In, L.³

10
- 65949118995
- M. Ueki S. Watanabe R. Yamanaka M. Ohta O. Okunaka Pept. Sci. 1999 117 120
- (1999) Pept. Sci. , pp. 117-120
- Ueki, M.¹ Watanabe, S.² Yamanaka, R.³ Ohta, M.⁴ Okunaka, O.⁵

11
- 0035847257
- The less general Fmoc/benzyl SPPS strategy, using an azidomethyl phenol protected Fmoc-Tyr-OH building block, 4a for the synthesis of sulfated PSGL-1 octapeptides may be problematic in asparagine and glutamine containing peptides leading e.g. to aspartimide formation and subsequent rearrangement -10
- K. Kitagawa C. Aida H. Fujiwara T. Yagami S. Futaki M. Kogire J. Ida K. Inoue J. Org. Chem. 2001 66 1 10
- (2001) J. Org. Chem. , vol.66 , pp. 1
- Kitagawa, K.¹ Aida, C.² Fujiwara, H.³ Yagami, T.⁴ Futaki, S.⁵ Kogire, M.⁶ Ida, J.⁷ Inoue, K.⁸

12
- 0020040553
- C. Unsworth J. Hughes Nature 1982 295 519 522
- (1982) Nature , vol.295 , pp. 519-522
- Unsworth, C.¹ Hughes, J.²

13
- 0842285220
- Y. Liu I. F. Lien S. Ruttgaizer P. Dove S. D. Taylor Org. Lett. 2004 6 209 212
- (2004) Org. Lett. , vol.6 , pp. 209-212
- Liu, Y.¹ Lien, I.F.² Ruttgaizer, S.³ Dove, P.⁴ Taylor, S.D.⁵

14
- 65949092077
- The 2,2,2-trichloroethyl sulfate ester containing peptides are very stable during HPLC analysis and purification with the standard water-acetonitrile-TFA buffers
- The 2,2,2-trichloroethyl sulfate ester containing peptides are very stable during HPLC analysis and purification with the standard water-acetonitrile-TFA buffers

15
- 85004724143
- S. Ram R. E. Ehrenkaufer Synthesis 1988 91 95
- (1988) Synthesis , pp. 91-95
- Ram, S.¹ Ehrenkaufer, R.E.²

16
- 66449125403
- 10.1074/jbc.M808179200
- J. H. Ippel C. J. C. de Haas A. Bunschoten J. A. G. van Strijp J. A. W. Kruijtzer R. M. J. Liskamp J. Kemmink J. Biol. Chem. 2009 10.1074/jbc.M808179200
- (2009) J. Biol. Chem.
- Ippel, J.H.¹ De Haas, C.J.C.² Bunschoten, A.³ Van Strijp, J.A.G.⁴ Kruijtzer, J.A.W.⁵ Liskamp, R.M.J.⁶ Kemmink, J.⁷

17
- 0035821247
- In contrast to His(Trt), Cys(Trt) is expected to be stable under the used 2-Cl Trt deprotection conditions: -1065
- M. Farzan C. E. Schnitzler N. Vasilieva D. Leung J. Kuhn C. Gerard N. P. Gerard H. Choe J. Exp. Med. 2001 193 1059 1065
- (2001) J. Exp. Med. , vol.193 , pp. 1059
- Farzan, M.¹ Schnitzler, C.E.² Vasilieva, N.³ Leung, D.⁴ Kuhn, J.⁵ Gerard, C.⁶ Gerard, N.P.⁷ Choe, H.⁸

18
- 0029874669
- K. Barlos D. Gatos O. Hatzi N. Koch S. Koutsogianni Int. J. Pept. Protein Res. 1996 47 148 153
- (1996) Int. J. Pept. Protein Res. , vol.47 , pp. 148-153
- Barlos, K.¹ Gatos, D.² Hatzi, O.³ Koch, N.⁴ Koutsogianni, S.⁵

19
- 0037587288
- S. Zaramella R. Strömberg E. Yeheskiely Eur. J. Org. Chem. 2003 2454 2461
- (2003) Eur. J. Org. Chem. , pp. 2454-2461
- Zaramella, S.¹ Strömberg, R.² Yeheskiely, E.³

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