Application of gel-phase 19F NMR spectroscopy for optimization of solid-phase synthesis of a hydrophobic peptide from the signal sequence of the mucin MUC1

Journal of Peptide Science

Volumn 13, Issue 5, 2007, Pages 354-361

  Pudelko, Maciej ^a   Kihlberg, Jan ^a,b   Elofsson, Mikael ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

Difficult sequence; Gel phase 19F NMR; Pseudo proline; Solid phase peptide synthesis

Indexed keywords

DIPEPTIDE; LEUCINE; MUCIN 1; PROLINE; THREONINE;

AMINO ACID SEQUENCE; ARTICLE; CONTROLLED STUDY; GEL; HYDROPHOBICITY; INTERMETHOD COMPARISON; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN STRUCTURE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SIGNAL TRANSDUCTION; SOLID PHASE SYNTHESIS; TANDEM REPEAT;

ANTIGENS, NEOPLASM; HUMANS; MUCINS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOPEPTIDES; PROTEIN SORTING SIGNALS;

EID: 34248575044     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.850     Document Type: Article

References (54)

1. Taylor-Papadimitriou J, Gendler SJ. Structure, biology and possible clinical applications of carcinoma-associated mucins (review). Int. J. Oncol. 1992; 1: 9-16.
2. Girling A, Bartkova J, Burchell J, Gendler SJ, Gillett C, Taylor-Papadimitriou J. A core protein epitope of the pem mucin detected by the monoclonal antibody sm-3 is selectively exposed in a range of primary carcinomas. Int. J. Cancer 1989; 43: 1072-1076.
3. Taylor-Papadimitriou J, Burchell JM, Plunkett T, Graham R, Correa I, Miles D, Smith M. Muc1 and the immunobiology of cancer. J. Mammary Gland Biol. Neoplasia 2002; 7: 209-221.
4. Heukamp LC, van Hall T, Ossendorp F, Burchell JM, Melief CJM, Taylor-Papadimitriou J, Offringa R. Effective immunotherapy of cancer in muc1-transgenic mice using clonal cytotoxic t lymphocytes directed against an immunodominant muc1 epitope. J. Immunother. 2002; 25: 46-56.
5. Taylor-Papadimitriou J, Burchell J, Miles DW, Dalziel M. Muc1 and cancer. Biochim. Biophys. Acta 1999; 1455: 301-313.
6. Hanisch F-G. Design of a muc1-based cancer vaccine. Biochem. Soc. Trans. 2005; 33: 705-708.
7. Brossart P, Heinrich KS, Stuhler G, Behnke L, Reichardt VL, Stevanovic S, Muhm A, Rammensee H-G, Kanz L, Brugger W. Identification of HLA-A2-restricted T-cell epitopes derived from the muc1 tumor antigen for broadly applicable vaccine therapies. Blood 1999; 93: 4309-4317.
8. Correa I, Plunkett T, Coleman J, Galani E, Windmill E, Burchell JM, Taylor-Papadimitriou J. Responses of human T cells to peptides flanking the tandem repeat and overlapping the signal sequence of muc1. Int. J. Cancer 2005; 115: 760-768.
9. Nicolaou KC, Pfefferkorn JA. Solid phase synthesis of complex natural products and libraries thereof. Biopolymers (Pept. Sci.) 2001; 60: 171-193.
10. Breinbauer R, Manger M, Scheck M, Waldmann H. Natural products guided compound library development. Curr. Med. Chem. 2002; 9: 2129-2145.
11. Shin DS, Kim DH, Chung WJ, Lee YS. Combinatorial solid phase peptide synthesis and bioassays. J. Biochem. Mol. Biol. 2005; 38: 517-525.
12. Liu M, Barany G, Live D. Parallel solid-phase synthesis of mucin-like glycopeptides. Carbohydr. Res. 2005; 340: 2111-2122.
13. Seeberger PH, Werz DB. Automated synthesis of oligosaccharides as a basis for drug discovery. Nat. Rev. Drug Discov. 2005; 4: 751-763.
14. Dettin M, Pegoraro S, Rovero P, Bicciato S, Bagno A, Di Bello C. Spps of difficult sequences-a comparison of chemical conditions. synthetic strategies and on-line monitoring. J. Pept. Res. 1997; 49: 103-111.
15. Bedford J, Hyde C, Johnson T, Jun W, Owen D, Quibell M, Sheppard RC. Amino acid structure and "Difficult sequences" In solid phase peptide synthesis. Int. J. Pept. Protein Res. 1992; 40: 300-307.
16. Hyde C, Johnson T, Owen D, Quibell M, Sheppard RC. Some 'difficult sequences' made easy. Int. J. Pept. Protein Res. 1994; 43: 431-440.
17. Milton RCL, Milton SCF, Adams PA. Prediction of difficult sequences in solid-phase peptide synthesis. J. Am. Chem. Soc. 1990; 112: 6039-6046.
18. Cremer G-A, Tariq H, Delmas AF. Combining a polar resin and a pseudo-proline to optimize the solid-phase synthesis of a 'difficult sequence'. J. Pept. Sci. 2006; 12: 437-442.
19. Kent SBH. Chemical synthesis of peptides and proteins. Annu. Rev. Biochem. 1988; 57: 957-989.
20. Larsen BD, Holm A. Incomplite fmoc deprotection in solid-phase synthesis of peptides. Int. J. Pept. Protein Res. 1994; 43: 1-9.
21. Fontenot JD, Ball JJ, Miller MA, David CM, Montelaro RC. A survey of potential problems and quality control in peptide synthesis by the fluorenylmethoxycarbonyl procedure. Pept. Res. 1991; 4: 19-25.
22. Wade JD, Bedford J, Sheppard RC, Tregear GW. DBU as an N-deprotecting reagent for the fluorenylmethoxycarbonyl group in continuous flow solid-phase peptide synthesis. Pept. Res. 1991; 4: 194-199.
23. Wade JD, Mathieu MN, Macris M, Tregear GW. Base-induced side reactions in fmoc-solid phase peptide synthesis: Minimization by use of piperazine as n-alpha-deprotection reagent. Lett. Pept. Sci. 2000; 7: 107-112.
24. Milton SCF, Milton RCL. An improved solid-phase synthesis of a difficult-sequence peptide using hexafluoro-2-propanol. Int. J. Pept. Protein Res. 1990; 36: 193-196.
25. Beyermann M, Bienert M. Synthesis of difficult peptide sequences: A comparison of fmoc- and boc-techniques. Tetrahedron Lett. 1992; 33: 3745-3748.
26. Hyde C, Johnson T, Sheppard RC. Internal aggregation during solid phase peptide synthesis. Dimethyl sulfoxide as a powerful dissociating solvent. J. Chem. Soc., Chem. Commun. 1992; 1573-1575.
27. Thaler A, Seebach D, Cardinaux F. Lithium-salt effects in peptide synthesis, improvement of degree of resin swelling and of efficiency of coupling in solid-phase synthesis. Helv. Chim. Acta 1991; 74: 628-643.
28. Ajikumar PK, Devaky KS. Solid phase synthesis of hydrophobic difficult sequence peptides on bddma-ps support. J. Pept. Sci. 2001; 7: 641-649.
29. Johnson T, Quibell M, Owen D, Sheppard RC. A reversible protecting group for the amide bond in peptides. Use in the synthesis of 'difficult sequences'. J. Chem. Soc., Chem. Commun. 1993; 369-372.
30. Toniolo C, Bonora GM, Mutter M, Pillai VNR. Linear oligopeptides 78. The effect of the insertion of a proline residue on the solution conformation of host peptides. Makromol. Chem. 1981; 182: 2007-2014.
31. Wöhr T, Mutter M. Pseudo-prolines in peptide synthesis: direct insertion of serine and threonine derived oxazolidines in dipeptides. Tetrahedron Lett. 1995; 36: 3847-3848.
32. Mutter M, Nefzi A, Sato T, Sun X, Wahl F, Wöhr T. Pseudo-prolines (Psi-pro) for accesing "Inaccessible" Peptides. Pept. Res. 1995; 8: 145-153.
33. Sampson WR, Patsiouras H, Ede NJ. The synthesis of "Difficult" Peptides using 2-hydroxy-4-methoxybenzyl or pseudoproline amino acid building blocks: A comparative study. J. Pept. Sci. 1999; 5: 403-409.
34. Kaiser E, Colescott RL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34: 595-598.
35. Krchnak V, Vagner J, Safar P, Lebl M. Noninvasive continuous monitoring of solid-phase peptide synthesis by acid-base indicator. Collect. Czech. Chem. Commun. 1988; 53: 2542-2548.
36. Talbo G, Wade JD, Dawson N, Manoussios M, Tregear GW. Rapid semi-on-line monitoring of fmoc solid-phase peptide synthesis by matrix-assisted laser desorption/ionization mass spectrometry. Lett. Pept. Sci. 1997; 4: 121-127.
37. Carrasco MR, Fitzgerald MC, Oda Y, Kent SBH. Direct monitoring of organic reactions on polymeric support. Tetrahedron Lett. 1997; 38: 6331-6334.
38. Bing Y. Monitoring the progress and the yield of solid phase organic reactions directly on resin support. Acc. Chem. Res. 1998; 31: 621-630.
39. Huber W, Bubendorf A, Grieder A, Obrecht D. Monitoring solid phase synthesis by infrared spectroscopic techniques. Anal. Chim. Acta 1999; 393: 213-221.
40. Seeberger PH, Beebe X, Sukenick GD, Pochapsky S, Danishefsky SJ. Monitoring the progress of solid-phase oligosaccharide synthesis by high-resolution magic angle spinning nmr: Observations of enhanced selectivity for alpha-glycoside formation from alpha-1,2-anhydrosugar donors in solid-phase couplings. Angew. Chem., Int. Ed. Engl. 1997; 36: 491-493.
41. Rousselot-Pailley P, Ede NJ, Lippens G. Monitoring of solid-phase organic synthesis on macroscopic supports by high-resolution magic angle spinning NMR. J. Comb. Chem. 2001; 3: 559-563.
42. Dal Cin M, Davalli S, Marchioro C, Passarini M, Perini O. Provera S, Zaramella A. Analytical methods for the monitoring of solid phase organic synthesis. Farmaco 2002; 57: 497-510.
43. 19F NMR spectroscopy to establish conditions for solid-phase synthesis of pilicise libraries. J. Comb. Chem. 2000; 2: 736-748.
44. 19F NMR spectroscopy. J. Comb. Chem. 2000; 2: 8-9.
45. 19F NMR spectral quality for resins commonly used in solid-phase organic synthesis; a study of peptide solid-phase glycosylations. Org. Biomol. Chem 2004; 2: 1770-1776.
46. 19F NMR spectrometry monitoring of reactions. J. Comb. Chem. 2005; 7: 285-297.
47. 19F NMR spectroscopy. Chembiochem 2002; 3: 1266-1269.
48. Vaino AR, Janda KD. Solid-phase organic synthesis: A critical understanding of the resin. J. Comb. Chem. 2000; 2: 579-596.
49. Dumy P, Keller M, Ryan DE, Rohwedder B, Wöhr T, Mutter M. Pseudo-prolines as a molecular hinge: Reversible induction of cis amide bond into peptide backbones. J. Am. Chem. Soc. 1997; 119: 918-925.
50. Kates SA, Sole NA, Beyermann M, Barany G, Albericio F. Optimized preparation of deca(L-alanyl)-L-valinamide by 9-fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis on polyethylene glycol-polystyrene (PEG-PS) graft supports, with 1,8-diazobicyclo(5.4.0)-undec-7-ene (DBU) deprotection. Pept. Res. 1996; 9: 106-113.
51. Tickler AK, Barrow CJ, Wade JD. Improved preparation of amyloid-beta peptides using DBU as N-Fmoc deprotection reagent. J. Pept. Sci. 2001; 7: 488-494.
52. Wallner FR, Elofsson M. NMR tube filter reactor for solid-phase synthesis and gel-phase F-19 NMR spectroscopy J. Comb. Chem. 2006; 8: 150-152.
53. Rink H. Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenyl-methylester resin. Tetrahedron Lett. 1987; 28: 3787-3790.
54. Krchnak V, Vagner J. Color-monitored solid-phase multiple peptide synthesis under low-pressure continuous-flow conditions. Pept. Res. 1990; 3: 182-193.