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

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

Author Souza, Sinval Estevam Gregorio de Autor UNIFESP Google Scholar
Malavolta, Luciana Autor UNIFESP Google Scholar
Cilli, Eduardo Maffud Autor UNIFESP Google Scholar
Schreier, Shirley Autor UNIFESP Google Scholar
Jubilut, Guita Nicolaewsky Autor UNIFESP Google Scholar
Nakaie, Clovis Ryuichi Autor UNIFESP Google Scholar
Institution Universidade Federal de São Paulo (UNIFESP)
Santa Casa Sao Paulo Sch Med Sci
Universidade de São Paulo (USP)
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.
Keywords Copolymer
electron paramagnetic resonance
peptide-resin cleavage
peptide synthesis
spin label
Language English
Sponsor Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
Date 2015-01-01
Published in Protein And Peptide Letters. Sharjah: Bentham Science Publ Ltd, v. 22, n. 5, p. 392-401, 2015.
ISSN 0929-8665 (Sherpa/Romeo, impact factor)
Publisher Bentham Science Publ Ltd
Extent 392-401
Access rights Closed access
Type Article
Web of Science ID WOS:000354338300002

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