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

Show simple item record

dc.contributor.author Souza, Sinval Estevam Gregorio de [UNIFESP]
dc.contributor.author Malavolta, Luciana [UNIFESP]
dc.contributor.author Cilli, Eduardo Maffud [UNIFESP]
dc.contributor.author Schreier, Shirley [UNIFESP]
dc.contributor.author Jubilut, Guita Nicolaewsky [UNIFESP]
dc.contributor.author Nakaie, Clovis Ryuichi [UNIFESP]
dc.date.accessioned 2018-06-18T11:27:17Z
dc.date.available 2018-06-18T11:27:17Z
dc.date.issued 2015-01-01
dc.identifier http://dx.doi.org/10.2174/0929866522666150206170329
dc.identifier.citation Protein And Peptide Letters. Sharjah: Bentham Science Publ Ltd, v. 22, n. 5, p. 392-401, 2015.
dc.identifier.issn 0929-8665
dc.identifier.uri http://repositorio.unifesp.br/11600/45152
dc.description.abstract Differently 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.sponsorship Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorship Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.format.extent 392-401
dc.language.iso eng
dc.publisher Bentham Science Publ Ltd
dc.relation.ispartof Protein And Peptide Letters
dc.rights Acesso restrito
dc.subject Copolymer en
dc.subject electron paramagnetic resonance en
dc.subject methylbenzhydrylamine-resin en
dc.subject peptide-resin cleavage en
dc.subject peptide synthesis en
dc.subject polymer en
dc.subject resin en
dc.subject spin label en
dc.title Novel Copoly(Styrene-Divinylbenzene)-Resins with Different Phenylmethylamine Groups for Use in Peptide Synthesis Method en
dc.type Artigo
dc.contributor.institution Universidade Federal de São Paulo (UNIFESP)
dc.contributor.institution Santa Casa Sao Paulo Sch Med Sci
dc.contributor.institution Unesp
dc.contributor.institution Universidade de São Paulo (USP)
dc.description.affiliation Univ Fed Sao Paulo, Paulista Med Sch, Dept Biophys, BR-04044020 Sao Paulo, SP, Brazil
dc.description.affiliation Santa Casa Sao Paulo Sch Med Sci, Dept Physiol Sci, BR-01221020 Sao Paulo, SP, Brazil
dc.description.affiliation Unesp, Inst Chem, Dept Biochem & Chem Technol, BR-1480090 Araraquara, SP, Brazil
dc.description.affiliation Univ Sao Paulo, Inst Chem, Dept Biochem, BR-05513970 Sao Paulo, Brazil
dc.description.affiliationUnifesp Univ Fed Sao Paulo, Paulista Med Sch, Dept Biophys, BR-04044020 Sao Paulo, SP, Brazil
dc.identifier.doi 10.2174/0929866522666150206170329
dc.description.source Web of Science
dc.identifier.wos WOS:000354338300002



File

File Size Format View

There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record

Search


Browse

Statistics

My Account