Artículo

Giudicessi, S.L.; Gurevich-Messina, J.M.; Martínez-Ceron, M.C.; Erra-Balsells, R.; Albericio, F.; Cascone, O.; Camperi, S.A. "Friendly strategy to prepare encoded one bead-one compound cyclic peptide library" (2013) ACS Combinatorial Science. 15(10):525-529
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Abstract:

One bead-one peptide libraries allow the screening of suitable ligands for any target protein. Short cyclic peptides are ideal ligands for affinity chromatography because of their high affinity and selectivity for the target protein and stability against proteases. We designed a library synthesis strategy to facilitate the identification of cyclic peptides by MS consisting of (a) sequential incorporation of a mixture of Fmoc-Ala-OH and Fmoc-Asp[2-phenylisopropyl (OPp)]-OH (15:85) to Gly-oxymethylbenzamide- ChemMatrix (Gly-HMBA-CM) resin, (b) synthesis of the combinatorial library on the resin by the divide-couple-recombine method, (c) removal of OPp with 4% TFA, (d) peptide cyclization on solid phase through side-chain Asp and amino terminus, and (e) removal of side chain protecting groups with a 95% TFA cocktail. Peptides were cleaved from the beads with ammonia and the linear code was sequenced by MALDI-TOF MS/MS. The high capacity of ChemMatrix resin together with the sensitivity of MS allows code sequencing from a single bead. © 2013 American Chemical Society.

Registro:

Documento: Artículo
Título:Friendly strategy to prepare encoded one bead-one compound cyclic peptide library
Autor:Giudicessi, S.L.; Gurevich-Messina, J.M.; Martínez-Ceron, M.C.; Erra-Balsells, R.; Albericio, F.; Cascone, O.; Camperi, S.A.
Filiación:Cathedra of Industrial Microbiology and Biotechnology, School of Pharmacy and Biochemistry, University of Buenos Aires, Junín 956, (1113) Buenos Aires, Argentina
National Scientific and Technological Research Council (CONICET), Rivadavia 1917, (1033) Buenos Aires, Argentina
CIHDECAR-CONICET, Department of Organic Chemistry, University of Buenos Aires, (1428) Buenos Aires, Argentina
Institute for Research in Biomedicine, Baldiri Reixac 10, (08028) Barcelona, Spain
Department of Organic Chemistry, University of Barcelona, Martí i Franquès 1-11, (08028) Barcelona, Spain
CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicin e, Barcelona Science Park, Baldiri Reixac 10, (08028) Barcelona, Spain
School of Chemistry and Physics, University of KwaZulu-Natal, University Road Westville 3630, Durban 4001, South Africa
Palabras clave:2-phenylisopropyl; 4-hydroxymethylbenzoic acid; affinity; ChemMatrix resin; combinatorial chemistry; MALDI-TOF MS/MS; peptide sequencing; solid phase; solid-phase synthesis; cyclopeptide; peptide library; chemistry; combinatorial chemistry; peptide library; synthesis; Combinatorial Chemistry Techniques; Peptide Library; Peptides, Cyclic
Año:2013
Volumen:15
Número:10
Página de inicio:525
Página de fin:529
DOI: http://dx.doi.org/10.1021/co400039a
Título revista:ACS Combinatorial Science
Título revista abreviado:ACS Combi. Sci.
ISSN:21568952
CODEN:ACSCC
CAS:Peptide Library; Peptides, Cyclic
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_21568952_v15_n10_p525_Giudicessi

Referencias:

  • Camperi, S.A., Martínez-Ceron, M.C., Giudicessi, S.L., Marani, M.M., Albericio, F., Cascone, O., Peptide affinity chromatography based on combinatorial strategies for protein purification (2013) Methods in Molecular Biology: Protein Downstream Processing, , In; Labrou, N. Humana Press, Inc. Springer: New York
  • Huang, P.Y., Carbonell, R.G., Affinity purification of proteins using ligands derived from peptide libraries (1995) Biotechnol. Bioeng., 47, pp. 288-297
  • Adessi, C., Soto, C., Converting a peptide into a drug: Strategies to improve stability and bioavailability (2002) Curr. Med. Chem., 9, pp. 963-978
  • Furka, A., Sebestyén, F., Asgedom, M., Dibó, G., General method for rapid synthesis of multicomponent peptide mixtures (1991) Int. J. Pep. Protein Res., 37, pp. 487-493
  • Lam, K.S., Salmon, S.E., Hersh, E.M., Hruby, V.J., Kazmierski, W.M., Knapp, R.J., A new type of synthetic peptide library for identifying ligand-binding activity (1991) Nature, 354, pp. 82-84
  • Steen, H., Mann, M., The ABC's (and XYZ's) of peptide sequencing (2004) Nat. Rev. Mol. Cell Biol., 5, pp. 699-711
  • Redman, J.E., Wilcoxen, K.M., Ghadiri, M.R., Automated mass spectrometric sequence determination of cyclic peptide library members (2003) J. Comb. Chem., 5, pp. 33-40
  • Bédard, F., Girard, A., Biron, E., A convenient approach to prepare topologically segregated bilayer beads for one-bead two-compound combinatorial peptide libraries (2013) Int. J. Pept. Res. Ther., 19, pp. 13-23
  • Simpson, L.S., Kodadek, T., Cleavable scaffold strategy for the synthesis of one-bead one-compound cyclic peptoid libraries that can be sequenced by tandem mass spectrometry (2012) Tetrahedron Lett., 53, pp. 2341-2344
  • Liu, T., Joo, S.H., Voorhees, J.L., Brooks, C.L., Pei, D., Synthesis and screening of a cyclic peptide library: Discovery of small-molecule ligands against human prolactin receptor (2009) Bioorg. Med. Chem., 17, pp. 1026-1033
  • Joo, S.H., Xiao, Q., Ling, Y., Gopishetty, B., Pei, D., High-throughput sequence determination of cyclic peptide library members by partial Edman degradation/mass spectrometry (2006) J. Am. Chem. Soc., 128, pp. 13000-13009
  • Franz, A.H., Liu, R., Song, A., Lam, K.S., Lebrilla, C.B., High-throughput one-bead-one-compound approach to peptide-encoded combinatorial libraries: MALDI-MS analysis of single TentaGel beads (2003) J. Comb. Chem., 5, pp. 125-137
  • Kappel, J.C., Barany, G., Methionine anchoring applied to solid phase synthesis of lysine-containing head-to-tail cyclic peptides (2003) Lett. Pept. Sci., 10, pp. 119-125
  • Youngquist, R.S., Fuentes, G.R., Lacey, M.P., Keough, T., Generation and screening of combinatorial peptide libraries designed for rapid sequencing by mass spectrometry (1995) J. Am. Chem. Soc., 117, pp. 3900-3906
  • Hancock, W.S., Marshall, G.R., Cyanogen bromide as a cleavage procedure in solid phase peptide synthesis (1975) J. Am. Chem. Soc., 97, pp. 7488-7489
  • Atherton, E., Logan, C.J., Sheppard, R.C., Peptide synthesis. Part 2. Procedures for solid-phase synthesis using Nα-fluorenylmethoxycarbonylamino-acids on polyamide supports. Synthesis of substance P and of acyl carrier protein 65-74 decapeptide (1981) J. Chem. Soc., Perkin Trans. 1, 1, pp. 538-546
  • Camperi, S.A., Marani, M.M., Iannucci, N.B., Coîté, S., Albericio, F., Cascone, O., An efficient strategy for the preparation of one-bead-one-peptide libraries on a new biocompatible solid support (2005) Tetrahedron Lett., 46, pp. 1561-1564
  • Martínez-Ceron, M.C., Giudicessi, S.L., Marani, M.M., Albericio, F., Cascone, O., Erra-Balsells, R., Camperi, S.A., Sample preparation for sequencing hits from one-bead one-peptide combinatorial libraries by MALDI-TOF/TOF MS (2010) Anal. Biochem., 400, pp. 295-297
  • Blackburn, C., Kates, S.A., Solid-phase synthesis of cyclic homodetic peptides (1997) Solid-Phase Peptide Synthesis. Methods in Enzymology, 289, p. 175. , In, Fields, G. B. Academic Press: New York, vol - 198
  • Garcia-Martin, F., Quintanar-Audelo, M., Garcia-Ramos, Y., Cruz, L.J., Gravel, C., Furic, R., Coîte, S., Albericio, F., ChemMatrix, A poly(ethylene glycol)-based support for the solid-phase synthesis of complex peptides (2006) J. Comb. Chem., 8, pp. 213-220
  • Bray, A.M., Valerio, R.M., Maeji, N.J., Cleavage of resin-bound peptide esters with ammonia vapour. Simultaneous multiple synthesis of peptide amides (1993) Tetrahedron Lett., 34, pp. 4411-4414
  • McMurray, J.S., Solid phase synthesis of a cyclic peptide using fmoc chemistry (1991) Tetrahedron Lett., 32, pp. 7679-7682
  • Sieber, P., Der 2-trimethylsilyläthyl-rest als selektiv abspaltbare carboxy-schutzgruppe (1977) Helv. Chim. Acta, 60, pp. 2711-2716
  • Kates, S.A., Solé, N.A., Johnson, C.R., Hudson, D., Barany, G., Albericio, F., A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides (1993) Tetrahedron Lett., 34, pp. 1549-1552
  • Chan, W.C., Bycroft, B.W., Evans, D.J., White, P.D., A novel 4-aminobenzyl ester-based carboxy-protecting group for synthesis of atypical peptides by Fmoc-But solid-phase chemistry (1995) J. Chem. Soc., Chem. Commun., pp. 2209-2210
  • Yue, C., Thierry, J., Potier, P., 2-Phenyl isopropyl esters as carboxyl terminus protecting groups in the fast synthesis of peptide fragments (1993) Tetrahedron Lett., 34, pp. 323-326
  • Mellor, S.L., Welling, D.A., Fehrentz, J.A., Paris, M., Martinez, J., Ede, N.J., Bray, A.M., Bloomberg, G.B., Synthesis of modified peptides (2000) Fmoc Solid Phase Peptide Synthesis: A Practical Approach, p. 137. , In, Chan, W. C. White, P. D. Oxford University Press: New York - 181
  • Wellings, D.A., Atherton, E., Standard Fmoc protocols (1997) Solid Phase Peptide Synthesis. Methods in Enzymology, 289, p. 67. , In; Fields, G. B. Academic Press: New York, Vol. - 83
  • Gude, M., Ryf, J., White, P.D., An accurate method for the quantitation of Fmoc-derivatized solid phase supports (2002) Lett. Pept. Sci., 9, pp. 203-206

Citas:

---------- APA ----------
Giudicessi, S.L., Gurevich-Messina, J.M., Martínez-Ceron, M.C., Erra-Balsells, R., Albericio, F., Cascone, O. & Camperi, S.A. (2013) . Friendly strategy to prepare encoded one bead-one compound cyclic peptide library. ACS Combinatorial Science, 15(10), 525-529.
http://dx.doi.org/10.1021/co400039a
---------- CHICAGO ----------
Giudicessi, S.L., Gurevich-Messina, J.M., Martínez-Ceron, M.C., Erra-Balsells, R., Albericio, F., Cascone, O., et al. "Friendly strategy to prepare encoded one bead-one compound cyclic peptide library" . ACS Combinatorial Science 15, no. 10 (2013) : 525-529.
http://dx.doi.org/10.1021/co400039a
---------- MLA ----------
Giudicessi, S.L., Gurevich-Messina, J.M., Martínez-Ceron, M.C., Erra-Balsells, R., Albericio, F., Cascone, O., et al. "Friendly strategy to prepare encoded one bead-one compound cyclic peptide library" . ACS Combinatorial Science, vol. 15, no. 10, 2013, pp. 525-529.
http://dx.doi.org/10.1021/co400039a
---------- VANCOUVER ----------
Giudicessi, S.L., Gurevich-Messina, J.M., Martínez-Ceron, M.C., Erra-Balsells, R., Albericio, F., Cascone, O., et al. Friendly strategy to prepare encoded one bead-one compound cyclic peptide library. ACS Combi. Sci. 2013;15(10):525-529.
http://dx.doi.org/10.1021/co400039a