Slightly modifying pseudoproline dipeptides incorporation strategy enables solid phase synthesis of a 54 AA fragment of caveolin-1encompassing the intramembrane domain

Journal of Peptide Science

Volumn 16, Issue 2, 2010, Pages 98-104

  Coïc, Yves Marie ^a   Le Lan, Charlotte ^b   Neumann, Jean Michel ^b   Jamin, Nadége ^b   Baleux, Françoise ^a  

^a INSTITUT PASTEUR   (France)

^b SERVICE DE CHIMIE BIOORGANIQUE ET DE MARQUAGE   (France)

Author keywords

HATU; Intramembrane peptide; Mass deviation; Pseudoproline dipeptide; RP HPLC; Side reaction; SPPS; Truncated peptide

Indexed keywords

CAVEOLIN 1; DIPEPTIDE; PEPTIDE FRAGMENT; PROLINE;

ARTICLE; CHEMICAL REACTION; HYDROPHOBICITY; MOLECULAR WEIGHT; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN STRUCTURE; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; CAVEOLIN 1; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPEPTIDES; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE PROTEINS; MOLECULAR SEQUENCE DATA; PROLINE; THIAZOLES;

EID: 74749105870     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1203     Document Type: Article

References (23)

1. Josic D, Clifton JG, Kovac S, Hixson DC. Membrane proteins as diagnostic biomarkers and targets for new therapies. Curr. Opin. Mol. Ther. 2008; 10: 116-123.
2. Hopkins AL, Groom CR. The druggable genome. Nat. Rev. Drug. Discov. 2002; 1: 727-730.
3. Tan S, Tan HT, Chung MC. Membrane proteins and membrane proteomics. Proteomics 2008; 8: 3924-3932.
4. Johnson EC, Kent SB. Studies on the insolubility of a transmembrane peptide from signal peptide peptidase. J. Am. Chem. Soc. 2006; 128: 7140-7141.
5. Khemtemourian L, Lavielle S, Bathany K, Schmitter JM, Dufourc EJ. Revisited and large-scale synthesis and purification of the mutated andwild type neu/erbB-2 membrane-spanning segment. J. Pept. Sci. 2006; 12: 361-368.
6. Coïc YM, Vincent M, Gallay J, Baleux F, Mousson F, Beswick V, Neumann JM, de Foresta B. Single-spanning membrane protein insertion in membrane mimetic systems: role and localization of aromatic residues. Eur. Biophys. J. 2005; 35: 27-39.
7. Clayton D, Shapovalov G, Maurer JA, Dougherty DA, Lester HA, Kochendoerfer GG. Total chemical synthesis and electrophysiological characterization of mechanosensitive channels from Escherichia coli and Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 4764-4769.
8. Tiburu EK, Dave PC, Vanlerberghe JF, Cardon TB, Minto RE, Lorigan GA. An improved synthetic and purification procedure for the hydrophobic segment of the transmembrane peptide phospholamban. Anal. Biochem. 2003; 318: 146-151.
9. Sato T, Kawakami T, Akaji K, Konishi H, Mochizuki K, Fujiwara T, Akutsu H, Aimoto S. Synthesis of a membrane protein with two transmembrane regions. J. Pept. Sci. 2002; 8: 172-180.
10. WohrT, WahlF, NefziA, RohwedderB, SatoT, SunXC, MutterM. Pseudo-prolines as a solubilizing, structure-disrupting protection technique in peptide synthesis. J. Am. Chem. Soc. 1996; 118: 9218-9227.
11. Coin I, Beyermann M, Bienert M. Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences. Nat. Protoc. 2007; 2: 3247-3256.
12. Cremer GA, 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.
13. White P, Keyte JW, Bailey K, Bloomberg G. Expediting the Fmoc solid phase synthesis of long peptides through the application of dimethyloxazolidine dipeptides. J. Pept. Sci. 2004; 10: 18-26.
14. Goncalves V, Gautier B, Huguenot F, Leproux P, Garbay C, Vidal M, Inguimbert N. Total chemical synthesis of the D2 domain of human VEGF receptor 1. J. Pept. Sci. 2009; 15: 417-422.
15. SampsonWR, Patsourias 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.
16. Cohen AW, Hnasko R, Schubert W, Lisanti MP. Role of caveolae and caveolins in health and disease. Physiol. Rev. 2004; 84: 1341-1379.
17. Le Lan C, Neumann JM, Jamin N. Role of themembrane interface on the conformation of the caveolin scaffolding domain: a CD and NMR study. FEBS Lett. 2006; 580: 5301-5305.
18. Chan WC, White PD. Fmoc Solid Phase Peptide Synthesis. A Practical Approach. Oxford University Press: London, 2000.
19. Garcia-Martin F, White P, Steinauer R, Cote S, Tulla-Puche J, Albericio F. The synergy of ChemMatrix resin and pseudoproline building blocks renders RANTES, a complex aggregated chemokine. Biopolymers 2006; 84: 566-575.
20. Kates SA,McGuinness BF,Blackburn C, Griffin GW,Sole NA, Barany G, Albericio F. "High-load" polyethylene glycol-polystyrene (PEG-PS) graft supports for solid-phase synthesis. Biopolymers 1998; 47: 365-380.
21. Gausepohl H, Pieles U, Frank R. Schiff base analog formation during in situ activation by HBTU & TBTU. Peptides, Proceedings of the 12 American Peptide Symposium, Smith JA, Rivier JE, (eds). ESCOM: Leiden, 1992; 523-524.
22. Albericio F, Bofill JM, El-Faham A, Kates SA. Use of onium salt-based coupling reagents in peptide synthesis. J. Org. Chem. 1998; 63: 9678-9683.
23. Carpino LA, Imazumi H, El-FahamA, Ferrer FJ, Zhang C, Lee Y, Foxman BM, Henklein P, Hanay C, Mugge C, Wenschuh H, Klose J, BeyermannM, Bienert M. The uronium/guanidinium Peptide coupling reagents: finally the true uronium salts. Angew. Chem. Int. Ed. Engl. 2002; 41: 441-445.