Novel Copoly(Styrene-Divinylbenzene)-Resins with Different Phenylmethylamine Groups for Use in Peptide Synthesis Method

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dc.contributor.authorSouza, Sinval Estevam Gregorio de [UNIFESP]
dc.contributor.authorMalavolta, Luciana [UNIFESP]
dc.contributor.authorCilli, Eduardo Maffud [UNIFESP]
dc.contributor.authorSchreier, Shirley [UNIFESP]
dc.contributor.authorJubilut, Guita Nicolaewsky [UNIFESP]
dc.contributor.authorNakaie, Clovis Ryuichi [UNIFESP]
dc.contributor.institutionUniversidade Federal de São Paulo (UNIFESP)
dc.contributor.institutionSanta Casa Sao Paulo Sch Med Sci
dc.contributor.institutionUnesp
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2018-06-18T11:27:17Z
dc.date.available2018-06-18T11:27:17Z
dc.date.issued2015-01-01
dc.description.abstractDifferently than the 4-methylbenzhydrylamine-resin (MBHAR) which contains a methyl group coupled to the phenylmethylamine-functionalized copoly(styrene-divinilbenzene) structure, alternative resins containing the electron-donating 4-tert-butyl-(BUBHAR) or the electron-withdrawing 2-chloro-(ClBHAR) and 2,4-chloro-(diClBHAR) groups were developed as potential supports for carboxamide peptide synthesis. Initially, a time-course investigation of HF cleavage reaction (0 degrees C) with these resins bearing the vasoconstrictor angiotensin II (AngII, DRVYIHPF) or its Gly(8)-AngII analogue revealed that the peptide-BUBHAR linkage is much more labile than those with ClBHAR or diClBHAR. HF cleavage times of near 2 h or longer than 24 h were needed for complete removal of peptide chains from these two classes of resin, respectively. By including MBHAR and benzhydrylamine-resins (BHAR) in this comparative study, the decreasing order of acid stability of the peptidyl-resin linkage was diClBHAR > ClBHAR > BHAR > MBHAR similar to BUBHAR. The same stability order was observed for the HCl/ propionic acid hydrolysis reaction (130 degrees C) with the Phe-or Gly-resins. These findings thus suggest that ClBHAR and diClBHAR are not appropriate for use in peptide synthesis. Nevertheless, these supports could still be tested as stationary phases for affinity chromatography. When placed into more apolar solvents, the beads of all of these resins exhibited a greater swelling (as measured by a microscope) or higher mobility of the polymer matrix (as measured with EPR experiments using spin-labeled beads). Moreover, under the latter approach, BUBHAR displayed a comparatively higher solvation degree than did MBHAR (in DCM, DMF and NMP), with slightly higher peptide synthesis yields as well.en
dc.description.affiliationUniv Fed Sao Paulo, Paulista Med Sch, Dept Biophys, BR-04044020 Sao Paulo, SP, Brazil
dc.description.affiliationSanta Casa Sao Paulo Sch Med Sci, Dept Physiol Sci, BR-01221020 Sao Paulo, SP, Brazil
dc.description.affiliationUnesp, Inst Chem, Dept Biochem & Chem Technol, BR-1480090 Araraquara, SP, Brazil
dc.description.affiliationUniv Sao Paulo, Inst Chem, Dept Biochem, BR-05513970 Sao Paulo, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Paulista Med Sch, Dept Biophys, BR-04044020 Sao Paulo, SP, Brazil
dc.description.sourceWeb of Science
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.format.extent392-401
dc.identifierhttp://dx.doi.org/10.2174/0929866522666150206170329
dc.identifier.citationProtein And Peptide Letters. Sharjah: Bentham Science Publ Ltd, v. 22, n. 5, p. 392-401, 2015.
dc.identifier.doi10.2174/0929866522666150206170329
dc.identifier.issn0929-8665
dc.identifier.urihttp://repositorio.unifesp.br/handle/11600/45152
dc.identifier.wosWOS:000354338300002
dc.language.isoeng
dc.publisherBentham Science Publ Ltd
dc.relation.ispartofProtein And Peptide Letters
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subjectCopolymeren
dc.subjectelectron paramagnetic resonanceen
dc.subjectmethylbenzhydrylamine-resinen
dc.subjectpeptide-resin cleavageen
dc.subjectpeptide synthesisen
dc.subjectpolymeren
dc.subjectresinen
dc.subjectspin labelen
dc.titleNovel Copoly(Styrene-Divinylbenzene)-Resins with Different Phenylmethylamine Groups for Use in Peptide Synthesis Methoden
dc.typeinfo:eu-repo/semantics/article
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