Multicomponent synthesis of acylated short peptoids with antifungal activity against plant pathogens
In this article, we describe the synthesis of a small library of short peptoids composed of four glycine residues and acylated with a fatty acid that showed a remarkable in vitro activity against two fungal plant pathogens. Their straightforward synthesis implied two consecutive Ugi reactions and ca...
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2012
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| 008 | 190411s2012 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84858705925 | |
| 024 | 7 | |2 cas |a glycine, 56-40-6, 6000-43-7, 6000-44-8; Amines; Antifungal Agents; Peptoids | |
| 030 | |a MODIF | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Galetti, M.D. | |
| 245 | 1 | 0 | |a Multicomponent synthesis of acylated short peptoids with antifungal activity against plant pathogens |
| 260 | |c 2012 | ||
| 270 | 1 | 0 | |m Ramírez, J.A.; Departamento de Química Orgánica, UMYMFOR (CONICET - Facultad de Ciencias Exactas Y Naturales), Universidad de Buenos Aires, C1428EGA, Buenos Aires, Argentina; email: jar@qo.fcen.uba.ar |
| 504 | |a Savary, S., Teng, P.S., Willocquet, L., Nutter Jr., F.W., Quantification and modeling of crop losses: A review of purposes (2006) Annual Review of Phytopathology, 44, pp. 89-112. , DOI 10.1146/annurev.phyto.44.070505.143342 | ||
| 504 | |a Knight, S.C., Anthony, V.M., Brady, A.M., Greenland, A.J., Heaney, S.P., Murray, D.C., Powell, K.A., Youle, D., Rationale and perspectives on the development of fungicides (1997) Annual Review of Phytopathology, 35, pp. 349-372. , DOI 10.1146/annurev.phyto.35.1.349 | ||
| 504 | |a Brogden, K.A., Antimicrobial peptides: Pore formers or metabolic inhibitors in bacteria (2005) Nat Rev Microbiol, 3, pp. 238-250. , doi:10.1038/nrmicro1098 | ||
| 504 | |a Marcos, J.F., Muñoz, A., Pérez-Payá, E., Misra, S., López-García, B., Identification and rational design of novel antimicrobial peptides for plant protection (2008) Annu Rev Phytopathol, 46, pp. 273-330. , doi:10.1146/annurev.phyto.121307.094843 | ||
| 504 | |a Straus, S.K., Hancock, R.E.W., Mode of action of the new antibiotic for Gram-positive pathogens daptomycin: Comparison with cationic antimicrobial peptides and lipopeptides (2006) Biochimica et Biophysica Acta - Biomembranes, 1758 (9), pp. 1215-1223. , DOI 10.1016/j.bbamem.2006.02.009, PII S0005273606000435 | ||
| 504 | |a Makovitzki, A., Avrahami, D., Shai, Y., Ultrashort antibacterial and antifungal lipopeptides (2006) Proceedings of the National Academy of Sciences of the United States of America, 103 (43), pp. 15997-16002. , DOI 10.1073/pnas.0606129103 | ||
| 504 | |a Makovitzki, A., Viterbo, A., Brotman, Y., Chet, I., Shai, Y., Inhibition of fungal and bacterial plant pathogens in vitro and in planta with ultrashort cationic lipopeptides (2007) Applied and Environmental Microbiology, 73 (20), pp. 6629-6636. , DOI 10.1128/AEM.01334-07 | ||
| 504 | |a Zuckermann, R.N., Martin, E.J., Spellmeyer, D.C., Stauber, G.B., Shoemaker, K.R., Kerr, J.M., Figliozzi, G.M., Moos, W.H., Discovery of nanomolar ligands for 7-transmembrane G-protein-coupled receptors from a diverse N-(substituted)glycine peptoid library (1994) Journal of Medicinal Chemistry, 37 (17), pp. 2678-2685 | ||
| 504 | |a Shin, S.B.Y., Yoo, B., Todaro, L.J., Kirshenbaum, K., Cyclic peptoids (2007) Journal of the American Chemical Society, 129 (11), pp. 3218-3225. , DOI 10.1021/ja066960o | ||
| 504 | |a Masip, I., Cortes, N., Abad, M.-J., Guardiola, M., Perez-Paya, E., Ferragut, J., Ferrer-Montiel, A., Messeguer, A., Design and synthesis of an optimized positional scanning library of peptoids: Identification of novel multidrug resistance reversal agents (2005) Bioorganic and Medicinal Chemistry, 13 (6), pp. 1923-1929. , DOI 10.1016/j.bmc.2005.01.024 | ||
| 504 | |a Zuckermann, R.N., Kerr, J.M., Kent, S.B.H., Moos, W.H., Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis (1992) J Am Chem Soc, 114, pp. 10646-10647. , doi:10.1021/ja00052a076 | ||
| 504 | |a Chongsiriwatana, N.P., Miller, T.M., Wetzler, M., Vakulenko, S., Karlsson, A.J., Palecek, S.P., Mobashery, S., Barron, A.E., Short alkylated peptoid mimics of antimicrobial lipopeptides (2011) Antimicrob Agents Chemother, 55, pp. 417-420. , doi:10.1128/AAC.01080-10 | ||
| 504 | |a Dömling, A., Recent developments in isocyanide based multicomponent reactions in applied chemistry (2006) ChemRev, 106, pp. 17-89. , doi:10.1021/cr0505728 | ||
| 504 | |a Xu, P., Zhang, T., Wang, W., Zou, X., Zhang, X., Fu, Y., Synthesis of PNA monomers and dimers by ugi four-component reaction (2003) Synthesis, (8), pp. 1171-1176 | ||
| 504 | |a Rivera, D.G., Wessjohann, L.A., Supramolecular compounds from multiple ugi multicomponent macrocyclizations: Peptoid-based cryptands, cages, and cryptophanes (2006) Journal of the American Chemical Society, 128 (22), pp. 7122-7123. , DOI 10.1021/ja060720r | ||
| 504 | |a Vercillo, O.E., Andrade, C.K.Z., Wessjohann, L.A., Design and synthesis of cyclic RGD pentapeptoids by consecutive Ugi reactions (2008) Org Lett, 10, pp. 205-208. , doi:10.1021/ol702521g | ||
| 504 | |a Henze, M., Kreye, O., Brauch, S., Nitsche, C., Naumann, K., Wessjohann, L.A., Westermann, B., Photoaffinity-labeled peptoids and depsipeptides by multicomponent reactions (2010) Synthesis, 17, pp. 2997-3003. , doi:10.1055/s-0030-1258182 | ||
| 504 | |a Sui, Q., Borchardt, D., Rabenstein, D.L., Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids (2007) Journal of the American Chemical Society, 129 (39), pp. 12042-12048. , DOI 10.1021/ja0740925 | ||
| 504 | |a Heerma, W., Verluis, C., De Koster, C.G., Kruijtzer, J.A.W., Zigrovic, I., Liskamp, R.M.J., Comparing mass spectrometric characteristics of peptides and peptoids (1996) Rapid Commun Mass Spectrom, 10, pp. 459-464. , doi:10.1002/(SICI)1097-0231(19960315)10:4〈459::AID-RCM501〉3.0. CO;2-J | ||
| 504 | |a Roepstorff, P., Fohlman, J., Proposal for a common nomenclature for sequence ions in mass spectra of peptides (1984) Biomed Mass Spectrom, 11, p. 601. , doi:10.1002/bms.1200111109 | ||
| 504 | |a Jacob, M.R., Walker, L.A., Natural products and antifungal drug discovery (2005) Methods in Molecular Medicine, 118, pp. 83-110. , Ernst EJ, Rogers PD (eds) antifungal agents: methods and protocols 1st ed. Humana Press Inc, Totowa, NJ | ||
| 504 | |a Hadacek, F., Greger, H., Testing of antifungal natural products: Methodologies, comparability of results and assay choice (2000) Phytochemical Analysis, 11 (3), pp. 137-147. , DOI 10.1002/(SICI)1099-1565(200005/06)11:3<137::AID-PCA514>3.0. CO;2-I | ||
| 504 | |a Makovitzki, A., Viterbo, A., Brotman, Y., Chet, I., Shai, Y., Inhibition of fungal and bacterial plant pathogens in vitro and in planta with ultrashort cationic lipopeptides (2007) Applied and Environmental Microbiology, 73 (20), pp. 6629-6636. , DOI 10.1128/AEM.01334-07 | ||
| 504 | |a Shai, Y., Mode of action of membrane active antimicrobial peptides (2002) Pept Sci, 66, pp. 236-248. , doi:10.1002/bip.10260 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a In this article, we describe the synthesis of a small library of short peptoids composed of four glycine residues and acylated with a fatty acid that showed a remarkable in vitro activity against two fungal plant pathogens. Their straightforward synthesis implied two consecutive Ugi reactions and can be efficiently extended to the construction of highly diverse libraries. © 2011 Springer Science+Business Media B.V. |l eng | |
| 536 | |a Detalles de la financiación: PICT2008-1394 y PME 2007-354 | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, X-084, UBACyT X-029 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 0315, PIP 100516 | ||
| 536 | |a Detalles de la financiación: Acknowledgements This study was supported by grants from the Universidad de Buenos Aires (UBACyT X-029 and X-084), the Agen- cia Nacional de Promoción Científica y Técnica (ANPCyT PICT2008-1394 y PME 2007-354) and the Consejo Nacional de Investigaciones Científicas y Técnicas (PIP 0315 and PIP 100516). We are grateful to UMYMFOR (UBA-CONICET) for the analytical and spectroscopic determinations. | ||
| 593 | |a Departamento de Química Orgánica, UMYMFOR (CONICET - Facultad de Ciencias Exactas Y Naturales), Universidad de Buenos Aires, C1428EGA, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ACYLATED PEPTOIDS |
| 690 | 1 | 0 | |a ANTIFUNGAL |
| 690 | 1 | 0 | |a MULTICOMPONENT REACTION |
| 690 | 1 | 0 | |a PLANT PATHOGEN |
| 690 | 1 | 0 | |a GLYCINE |
| 690 | 1 | 0 | |a PEPTOID |
| 690 | 1 | 0 | |a ACYLATION |
| 690 | 1 | 0 | |a ANTIFUNGAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a ELECTROSPRAY MASS SPECTROMETRY |
| 690 | 1 | 0 | |a MINIMUM INHIBITORY CONCENTRATION |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PLANT DISEASE |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a UGI REACTION |
| 690 | 1 | 0 | |a ACYLATION |
| 690 | 1 | 0 | |a AMINES |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENTS |
| 690 | 1 | 0 | |a FUSARIUM |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MICROBIAL SENSITIVITY TESTS |
| 690 | 1 | 0 | |a PEPTOIDS |
| 690 | 1 | 0 | |a PLANTS |
| 690 | 1 | 0 | |a SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION |
| 700 | 1 | |a Cirigliano, A.M. | |
| 700 | 1 | |a Cabrera, G.M. | |
| 700 | 1 | |a Ramírez, Javier Alberto | |
| 773 | 0 | |d 2012 |g v. 16 |h pp. 113-119 |k n. 1 |p Mol. Diversity |x 13811991 |t Molecular Diversity | |
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