EPR investigation of the influence of side chain protecting groups on peptide-resin solvation of the Asx and Glx model containing peptides

dc.contributorUniversidade Estadual Paulista (UNESP)
dc.creatorCilli, Eduardo Maffud
dc.creatorVicente, Eduardo F.
dc.creatorCrusca, Edson
dc.creatorNakaie, Clovis R.
dc.date2014-05-20T15:24:46Z
dc.date2016-10-25T17:59:05Z
dc.date2014-05-20T15:24:46Z
dc.date2016-10-25T17:59:05Z
dc.date2007-07-30
dc.date.accessioned2017-04-05T23:49:02Z
dc.date.available2017-04-05T23:49:02Z
dc.identifierTetrahedron Letters. Oxford: Pergamon-Elsevier B.V., v. 48, n. 31, p. 5521-5524, 2007.
dc.identifier0040-4039
dc.identifierhttp://hdl.handle.net/11449/35312
dc.identifierhttp://acervodigital.unesp.br/handle/11449/35312
dc.identifier10.1016/j.tetlet.2007.05.164
dc.identifierWOS:000248527400036
dc.identifier0000-0002-4767-0904
dc.identifierhttp://dx.doi.org/10.1016/j.tetlet.2007.05.164
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/879070
dc.descriptionIn spite of all progressive efforts aiming to optimize SPPS, serious problems mainly affecting the assembly of aggregating sequences have persisted. Following the study intended to unravel the complex solvation phenomenon of peptide-resin beads, the XING and XAAAA model aggregating segments were labeled with a paramagnetic probe and studied via EPR spectroscopy. Low and high substituted resins were also comparatively used, with the X residue being Asx or Glx containing the main protecting groups used in the SPPS. Notably, the cyclo-hexyl group used for Asp and Glu residues in Boc-chemistry induced greater chain immobilization than its tert-butyl partner-protecting group of the Fmoc strategy. Otherwise, the most impressive peptide chain immobilization occurred when the large trytil group was used for Asn and Gln protection in Fmoc-chemistry. These surprising results thus seem to stress the possibility of the relevant influence of the amino-acid side chain protecting groups in the overall peptide synthesis yield. (C) 2007 Elsevier Ltd. All rights reserved.
dc.languageeng
dc.publisherElsevier B.V.
dc.relationTetrahedron Letters
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectsolid-phase peptide synthesis
dc.subjectdifficult sequences
dc.subjectaggregation
dc.subjectEPR
dc.subjectswelling
dc.titleEPR investigation of the influence of side chain protecting groups on peptide-resin solvation of the Asx and Glx model containing peptides
dc.typeOtro


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