Synthesis of an arginine tagged [Cys155-Arg180] fragment of NY-ESO-1: elimination of an undesired by-product using 'In house' resins

Synthesis

Volumn , Issue 20, 2009, Pages 3460-3466

  Harris, Paul W R ^a   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Arginine tag; Hmba linker; Resins; Solid phase

Indexed keywords

HMBA LINKER; PEPTIDE FRAGMENTS; SOLID PHASE SYNTHESIS; SOLID-PHASE;

AMINES; RESINS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

4 HYDROXYMETHYLBENZIOC ACID; 9 FLUORENYLMETHYL CHLOROFORMATE; AMIDE RESIN; AMINOMETHYL POLYSYTRENE RESIN; ARGININE; BENZOIC ACID DERIVATIVE; CYSTEINE; NY ESO 1 ANTIGEN; PEPTIDE FRAGMENT; RESIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL STRUCTURE; POLYMERIZATION; SOLID PHASE SYNTHESIS;

EID: 72049124583     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216952     Document Type: Article

References (29)

1. Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161.
2. Bouillon, I.; Sourai, M.; Miller, M. K.; Krchnak, V. J. Comb. Chem. 2009, 11, 213.
3. Pugh, K. C.; York, E. J.; Stewart, J. M. Int. J. Pept. Protein Res. 1992, 40, 208.
4. Wang, S.-S. J. Am. Chem. Soc. 1973, 95, 1328.
5. Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. Int. J. Pept. Protein Res. 1991, 37, 513.
6. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
7. Atherton, E.; Benoiton, N. L.; Brown, E.; Sheppard, R. C.; Williams, B. J. J. Chem. Soc., Chem. Commun. 1981, 336.
8. Atherton, E.; Logan, C. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 538.
9. (a) For Wang linker equivalents, see: Zinieris, N.; Kokinaki, S.; Leondiadis, L.; Ferderigos, N. Synlett 2006, 2789.
10. (b) For 2-Cl-trityl linker equivalents, see: Zikos, C.; Livaniuo, E.; Leondiadis, L.; Ferderigos, N.; Ithakissios, D. S.; Evangelatos, G. P. J. Pept. Sci. 2005, 8, 419.
11. (c) For Rink Amide linker equivalents, see: Bertnatowicz, M. S.; Daniels, S. B.; Koster, H. Tetrahedron Lett. 1989, 30, 4645.
12. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776.
13. Harris, P. W. R.; Brimble, M. A. manuscript in preparation.
14. (a) Atherton, E.; Logan, C. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 529.
15. (b) Choma, C. T.; Robillard, G. T.; Englebretsen, D. R. Tetrahedron Lett. 1998, 39, 2417.
16. Mellor, S. L.; Wellings, D. A.; Fehrentz, J.-A.; Paris, M.; Martinez, J.; Ede, N. J.; Bray, A. M.; Evans, D. J.; Bloomberg, G. B. In Fmoc solid phase peptide synthesis: a practical approach; Oxford University Press: Oxford, 2000, 145-149.
17. Rittel, W. R. Helv. Chim. Acta 1962, 45, 465.
18. 2O (95:2.5:2.5, v/v/v) gave identical HPLC and mass spectra to 6.
19. Sheppard et al. reported hydrolysis at the HMBA linker when attempting ammonolysis. This was determined to be due to moisture present in the resin, see: Brown, E.; Sheppard, R. C.; Williams, B. J. J. Chem. Soc., Perkin Trans. 1 1983, 75.
20. King, D. S.; Fields, C. G.; Fields, G. B. Int. J. Pept. Protein Res. 1999, 36, 255.
21. Reagent, R.; Albericio, F.; Kenib-Cordonier, N.; Bianaclanan, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. J. Org. Chem. 1990, 55, 3730.
22. Sole, N. A.; Barany, G. J. Org. Chem. 1992, 57, 5399.
23. Mitchell, A. R.; Kent, S. B. H.; Englenhard, M.; Merrifield, R. B. J. Org. Chem. 1978, 43, 2845.
24. Kent, S. B. H. personal communication.
25. (a) Albericio, F.; Barany, G. Int. J. Pept. Protein Res. 1985, 26, 92.
26. (b) NeoMPS S.A. International Patent Application W02005/095332, 2005.
27. 2 should be rejected. For commercially obtained Wang, Rink Amide AM, and 2-Cl trityl reins used here, the swelling was 6.1, 5 and 4.5 mL/g, respectively, while for the 'in house' reins 16 and 17, the swelling was 9 and 9.7 mL/g, respectively.
28. Harris, P. W. R.; Williams, G. M.; Shepherd, P.; Brimble, M. A. Int. J. Pept. Res. Ther. 2008, 14, 387.
29. Apffel, A.; Fischer, S.; Goldberg, G.; Goodley, P. C.; Kuhlmann, F. E. J. Chromatogr., A 1995, 712, 177.