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
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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
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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
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Volumen: | 15
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Número: | 10
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Página de inicio: | 525
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Página de fin: | 529
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DOI: |
http://dx.doi.org/10.1021/co400039a |
Título revista: | ACS Combinatorial Science
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Título revista abreviado: | ACS Combi. Sci.
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ISSN: | 21568952
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CODEN: | ACSCC
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CAS: | Peptide Library; Peptides, Cyclic
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_21568952_v15_n10_p525_Giudicessi |
Referencias:
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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