Native chemical ligation of hydrophobic peptides in organic solvents

Journal of Peptide Science

Volumn 16, Issue 10, 2010, Pages 558-562

  Dittmann, Marc ^a   Sauermann, Jörg ^a   Seidel, Ralf ^a   Zimmermann, Wolfgang ^b   Engelhard, Martin ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Hydrophobic peptides; Ligation in organic solvents; Peptide synthesis; Transmembrane proteins

Indexed keywords

N,N DIMETHYLFORMAMIDE; PEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLUBILITY;

DIMETHYLFORMAMIDE; PEPTIDES; SOLVENTS; WATER;

EID: 78149378385     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1285     Document Type: Article

References (26)

1. Wallin E, Heijne GV. Genome-wide analysis of integral membrane proteins from eubacterial, archaean, and eukaryotic organisms. Protein Sci. 1998; 7: 1029-1038.
2. Kent SBH. Total chemical synthesis of proteins. Chem. Soc. Rev. 2009; 38: 338-351.
3. Merrifield B. Solid phase synthesis. Nobel lecture, 8 December 1984. Biosci. Rep. 1985; 5: 353-376.
4. Dawson PE, Muir TW, Clark-Lewis I, Kent SBH. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-779.
5. Severinov K, Muir TW. Expressed protein ligation, a novel method for studying protein-protein interactions in transcription. J. Biol. Chem. 1998; 273: 16205-16209.
6. α thioester building blocks. Tetrahedron Lett. 2007; 48: 1795-1799.
7. Olschewski D, Becker CFW. Chemical synthesis and semisynthesis of membrane proteins. Mol. BioSyst. 2008; 4: 733-740.
8. Bollhaben R, Schmiedberger M, Grell E. High-performance liquid chromatographic purification of extremely hydrophobic peptides: transmembrane segments. J. Chromatogr. A 1995; 711: 181-186.
9. Kassim SY, Restrepo IM, Kalivretenos AG. Synthesis and purification of hydrophobic peptides for use in biomimetic ion channels. J. Chromatogr. A 1998; 816: 11-20.
10. Kochendoerfer GG, Salom D, Lear JD, Wilk-Orescan R, Kent SBH, DeGrado WF. Total chemical synthesis of the integral membrane protein influenza a virus M2: role of its C-terminal domain in tetramer assembly. Biochemistry 1999; 38: 11905-11913.
11. Valiyaveetil FI, MacKinnon R, Muir TW. Semisynthesis and folding of the potassium channel KcsA. J. Am. Chem. Soc. 2002; 124: 9113-9120.
12. Sato T, Saito Y, Aimoto S. Synthesis of the C-terminal region of opioid receptor like 1 in an SDS micelle by the native chemical ligation: effect of thiol additive and SDS concentration on ligation efficiency. J. Pept. Sci. 2005; 11: 410-416.
13. 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. USA 2004; 101: 4764-4769.
14. Otaka A, Ueda S, Tomita K, Yano Y, Tamamura H, Matsuzaki K, Fujii N. Facile synthesis of membrane-embedded peptides utilizing lipid bilayer-assisted chemical ligation. Chem. Commun. 2004; 1722-1723.
15. Hunter CL, Kochendoerfer GG. Native chemical ligation of hydrophobic peptides in lipid bilayer systems. Bioconjug. Chem. 2004; 15: 437-440.
16. Wegener AA, Klare JP, Engelhard M, Steinhoff HJ. Structural insights into the early steps of receptor-transducer signal transfer in archaeal phototaxis. EMBO J. 2001; 20: 5312-5319.
17. Gordeliy VI, Labahn J, Moukhametzianov R, Efremov R, Granzin J, Schlesinger R, Büldt G, Savopol T, Scheidig AJ, Klare JP, Engelhard M. Molecular basis of transmembrane signalling by sensory rhodopsin II-transducer complex. Nature 2002; 419: 484-487.
18. Klare JP, Chizhov I, Engelhard M. Microbial Rhodopsins: Scaffolds for Ion Pumps, Channels, and Sensors. In Bioenergetics Results and Problems in Cell Differentiation (45) Bioenergetics: Energy Conservation and Conversion, Schäfer G, Penefsky H (eds). Springer-Verlag: Berlin Heidelberg, 2008; 73-122.
19. Schnölzer M, Alewood P, Jones A, Alewood D, Kent SBH. In situ neutralization in Boc-chemistry solid phase petide synthesis. Int. J. Peptide Protein Res. 1992; 40: 180-193.
20. Hackeng TM, Griffin JH, Dawson PE. Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology. Proc. Natl. Acad. Sci. USA 1999; 96: 10068-10073.
21. Johnson ECB, Kent SBH. Studies on the insolubility of a transmembrane peptide from signal peptide peptidase. J. Am. Chem. Soc. 2006; 128: 7140-7141.
22. Johnson ECB, Kent BHK. Insights into the mechanism and catalysis of the native chemical ligation reaction. J. Am. Chem. Soc. 2006; 128: 6640-6646.
23. Mannila J, Järvinen K, Holappa J, Matilainen L, Auriola S, Jarho P. Cyclodextrins and chitosan derivatives in sublingual delivery of low solubility peptides: a study using cyclosporin A, α-cyclodextrin and quaternary chitosan N-betainate. Int. J. Pharm. 2009; 381: 19-24.
24. Seebach D, Thaler A, Beck AK. Solubilization of peptides in non-polar organic solvents by the addition of inorganic salts: facts and implications. Helv. Chim. Acta 1989; 72: 857-867.
25. Robey FA. Selective and facile cyclization of N-chloroacetylated peptides from the C4 domain of HIV Gp120 in LiCl/DMF solvent systems. J. Pept. Res. 2000; 56: 115-20.
26. Sagne C, Isambert M-F, Henry J-P, Gasnier B. SDS-resistant aggregation of membrane proteins: application to the purification of the vesicular monoamine transporter. Biochem. J. 1996; 316: 825-831.