One-bead, one-compound peptide library sequencing via high-pressure ammonia cleavage coupled to nanomanipulation/nanoelectrospray ionization mass spectrometry

Analytical Biochemistry

Volumn 398, Issue 1, 2010, Pages 7-14

  Brown, Jennifer M ^a   Hoffmann, William D ^a   Alvey, Cory M ^a   Wood, Addison R ^a   Verbeck, Guido F ^a   Petros, Robby A ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

HMBA; Mass spectrometry; OBOC peptide library; Peptide cleavage; Sequencing

Indexed keywords

AMINO ACIDS; AMMONIA; BENZOIC ACID; IONIZATION OF GASES; LIBRARIES; MASS SPECTROMETRY; MICROMANIPULATORS; NANOTECHNOLOGY; RESINS;

COMBINATORIAL PEPTIDE LIBRARIES; ENVIRONMENTALLY RESPONSIBLE; HMBA; IONIZATION MASS SPECTROMETRY; NANOELECTROSPRAY IONIZATION MASS SPECTROMETRY; PEPTIDE CLEAVAGES; PEPTIDE LIBRARY; SEQUENCING;

PEPTIDES;

AMINO ACID; AMMONIA; BENZOIC ACID; PEPTIDE; PEPTIDE LIBRARY; RESIN;

AMINO ACID SEQUENCE; ARTICLE; COMBINATORIAL LIBRARY; CONTROLLED STUDY; ISOLATION PROCEDURE; MASS SPECTROMETRY; NANOTECHNOLOGY; PRIORITY JOURNAL; PROTEIN CLEAVAGE; REPRODUCIBILITY; SCREENING;

EID: 73549102168     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2009.10.044     Document Type: Article

References (32)

1. Dolle R.E., Le Bourdonnec B., Goodman A.J., Morales G.A., Thomas C.J., and Zhang W. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2007. J. Comb. Chem. 10 (2008) 753-802
2. Aina O.H., Liu R.W., Sutcliffe J.L., Marik J., Pan C.X., and Lam K.S. From combinatorial chemistry to cancer-targeting peptides. Mol. Pharm. 4 (2007) 631-651
3. Kritzer J.A., Luedtke N.W., Harker E.A., and Schepartz A. A rapid library screen for tailoring β-peptide structure and function. J. Am. Chem. Soc. 127 (2005) 14584-14585
4. Thompson L.A., and Ellman J.A. Synthesis and applications of small molecule libraries. Chem. Rev. 96 (1996) 555-600
5. Lam K.S., Salmon S.E., Hersh E.M., Hruby V.J., Kazmierski W.M., and Knapp R.J. A new type of synthetic peptide library for identifying ligand-binding activity. Nature 354 (1991) 82-84
6. Houghten R.A., Pinilla C., Blondelle S.E., Appel J.R., Dooley C.T., and Cuervo J.H. Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery. Nature 354 (1991) 84-86
7. Furka A., Sebestyen F., Asgedom M., and Dibo G. General method for rapid synthesis of multicomponent peptide mixtures. Int. J. Pept. Protein Res. 37 (1991) 487-493
8. Lam K.S., Lebl M., and Krchnak V. The "one-bead-one-compound" combinatorial library method. Chem. Rev. 97 (1997) 411-448
9. Scott J.K., and Smith G.P. Searching for peptide ligands with an epitope library. Science 249 (1990) 386-390
10. Cwirla S.E., Peters E.A., Barrett R.W., and Dower W.J. Peptides on phage: a vast library of peptides for identifying ligands. Proc. Natl. Acad. Sci. USA 87 (1990) 6378-6382
11. Devlin J.J., Panganiban L.C., and Devlin P.E. Random peptide libraries: a source of specific protein binding molecules. Science 249 (1990) 404-406
12. Marani M.M., Oliveira E., Côté S., Camperi S.A., Albericio F., and Cascone O. Identification of protein-binding peptides by direct matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis of peptide beads selected from the screening of one bead-one peptide combinatorial libraries. Anal. Biochem. 370 (2007) 215-222
13. Camperi S.A., Marani M.M., Iannucci N.B., Côté S., Albericio F., and Cascone O. An efficient strategy for the preparation of one-bead-one-peptide libraries on a new biocompatible solid support. Tetrahedron Lett. 46 (2005) 1561-1564
14. Bray A.M., Valerio R.M., and Maeji N.J. Cleavage of resin-bound peptide esters with ammonia vapour: simultaneous multiple synthesis of peptide amides. Tetrahedron Lett. 34 (1993) 4411-4414
15. Atherton E., Gait M.J., Sheppard R.C., and Williams B.J. The polyamide method of solid phase peptide and oligonucleotide synthesis. Bioorg. Chem. 8 (1979) 351-370
16. Lee S.S., Lim J., Cha J., Tan S., and Heath J.R. Rapid microwave-assisted CNBr cleavage of bead-bound peptides. J. Comb. Chem. 10 (2008) 807-809
17. Schroeder W.A., Shelton J.B., and Shelton J.R. An examination of conditions for the cleavage of polypeptide chains with cyanogen bromide: application to catalase. Biochem. Biophys. 130 (1969) 551-556
18. Yu Z.G., and Chu Y.H. Combinatorial epitope search: pitfalls of library design. Bioorg. Med. Chem. Lett. 7 (1997) 95-98
19. Paulick M.G., Hart K.M., Brinner K.M., Tjandra M., Charych D.H., and Zuckermann R.N. Cleavable hydrophilic linker for one-bead-one-compound sequencing of oligomer libraries by tandem mass spectrometry. J. Comb. Chem. 8 (2006) 417-426
20. Holmes C.P., and Jones D.G. Reagents for combinatorial organic synthesis development of a new O-nitrobenzyl photolabile linker for solid-phase synthesis. J. Org. Chem. 60 (1995) 2318-2319
21. Thakkar A., Cohen A.S., Connolly M.D., Zuckermann R.N., and Pei D. High-throughput sequencing of peptoids and peptide-peptoid hybrids by partial Edman degradation and mass spectrometry. J. Comb. Chem. 11 (2009) 294-302
22. N.L. Ledbetter, B.L. Walton, P. Davila, W.D. Hoffmann, R.N. Ernest, G.F. Verbeck, Nanomanipulation coupled to nanospray mass spectrometry applied to the extraction and analysis of trace analytes found on fibers, J. Forens. Sci., in press.
23. Marani M.M., Ceron M.C.M., Giudicessi S.L., de Oliveira E., Côté S., Erra-Balsells R., Albericio F., Cascone O., and Camperi S.A. Screening of one-bead-one-peptide combinatorial library using red fluorescent dyes: presence of positive and false positive beads. J. Comb. Chem. 11 (2009) 146-150
24. Mellor S.L., Wellings D.A., Fehrentz J.-A., Paris M., Martinez J., Ede N.J., Bray A.M., Evans D.J., and Bloomberg G.B. Synthesis of modified peptides. In: Chan W.C., and White P.D. (Eds). Fmoc Solid Phase Peptide Synthesis (2000), Oxford University Press, New York 137-181
25. Bray A.M., Maeji N.J., Jhingran A.G., and Valerio R.M. Gas-phase cleavage of peptides from a solid support with ammonia vapor: application in simultaneous multiple peptide synthesis. Tetrahedron Lett. 32 (1991) 6163-6166
26. Bacsa B., Horváti K., Bõsze S., Andreae F., and Kappe C.O. Solid-phase synthesis of difficult peptide sequences at elevated temperatures: a critical comparison of microwave and conventional heating technologies. J. Org. Chem. 73 (2008) 7532-7542
27. Atherton E., Logan C.J., and Sheppard R.C. Peptide synthesis, part 2: procedures for solid-phase synthesis using N-α-fluorenylmethoxycarbonyl amino acids on polyamide supports: synthesis of substance P and of acyl carrier protein 65-74 decapeptide. J. Chem. Soc. Perkin Trans. 1 (1981) 538-546
28. Murray J.K., Sadowsky J.D., Scalf M., Smith L.M., Tomita Y., and Gellman S.H. Exploration of structure-activity relationships among foldamer ligands for a specific protein binding site via parallel and split-and-mix library synthesis. J. Comb. Chem. 10 (2008) 204-215
29. Murray J.K., Farooqi B., Sadowsky J.D., Scalf M., Freund W.A., Smith L.M., Chen J.D., and Gellman S.H. Efficient synthesis of a β-peptide combinatorial library with microwave irradiation. J. Am. Chem. Soc. 127 (2005) 13271-13280
30. Murray J.K., and Gellman S.H. Application of microwave irradiation to the synthesis of 14-helical β-peptides. Org. Lett. 7 (2005) 1517-1520
31. Hintersteiner M., Buehler C., Uhl V., Schmied M., Müller J., Kottig K., and Auer M. Confocal nanoscanning, bead picking (CONA): PickoScreen microscopes for automated and quantitative screening of one-bead one-compound libraries. J. Comb. Chem. 11 (2009) 286-294
32. Kinter M., and Sherman N.E. Protein Sequencing and Identification Using Tandem Mass Spectrometry (2000), John Wiley, New York