Comparative investigation of the cleavage step in the synthesis of model peptide resins: Implications for N-alpha-9-fluorenylmethyloxycarbonyl-solid phase peptide synthesis

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dc.contributor.author Jubilut, Guita Nicolaewsky [UNIFESP]
dc.contributor.author Cilli, Eduardo Maffud [UNIFESP]
dc.contributor.author Crusca Junior, Edson
dc.contributor.author Silva, Elias Horacio [UNIFESP]
dc.contributor.author Okada, Yoshio
dc.contributor.author Nakaie, Clovis Ryuichi [UNIFESP]
dc.date.accessioned 2016-01-24T12:41:54Z
dc.date.available 2016-01-24T12:41:54Z
dc.date.issued 2007-03-01
dc.identifier http://dx.doi.org/10.1248/cpb.55.468
dc.identifier.citation Chemical & Pharmaceutical Bulletin. Tokyo: Pharmaceutical Soc Japan, v. 55, n. 3, p. 468-470, 2007.
dc.identifier.issn 0009-2363
dc.identifier.uri http://repositorio.unifesp.br/handle/11600/29524
dc.description.abstract Based on our studies of the stability of model peptide-resin linkage in acid media, we previously proposed a rule for resin selection and a final cleavage protocol applicable to the N-alpha-tert-butyloxycarbonyl (Boc)-peptide synthesis strategy. We found that incorrect choices resulted in decreases in the final synthesis yield, which is highly dependent on the peptide sequence, of as high as 30%. the present paper continues along this line of research but examines the N-alpha-9-fluorenylmethyloxycarbonyl (Fmoc)-synthesis strategy. the vasoactive peptide angiotensin II (All, DRVYIHPF) and its [Gly(8)]-All analogue were selected as model peptide resins. Variations in parameters such as the type of spacer group (linker) between the peptide backbone and the resin, as well as in the final acid cleavage protocol, were evaluated. the same methodology employed for the Boc strategy was used in order to establish rules for selection of the most appropriate linker-resin conjugate or of the peptide cleavage method, depending on the sequence to be assembled. the results obtained after treatment with four cleavage solutions and with four types of linker groups indicate that, irrespective of the circumstance, it is not possible to achieve complete removal of the peptide chains from the resin. Moreover, the Phe-attaching peptide at the C-terminal yielded far less cleavage (50-60%.) than that observed with the Gly-bearing sequences at the same position (70-90%). Lastly, the fastest cleavage occurred with reagent K acid treatment and when the peptide was attached to the Wang resin. en
dc.format.extent 468-470
dc.language.iso eng
dc.publisher Pharmaceutical Soc Japan
dc.relation.ispartof Chemical & Pharmaceutical Bulletin
dc.rights Acesso aberto
dc.subject peptide synthesis en
dc.subject peptidyl resin en
dc.subject cleavage en
dc.subject linker group en
dc.title Comparative investigation of the cleavage step in the synthesis of model peptide resins: Implications for N-alpha-9-fluorenylmethyloxycarbonyl-solid phase peptide synthesis en
dc.type Artigo
dc.contributor.institution Universidade Federal de São Paulo (UNIFESP)
dc.contributor.institution Univ Estadual Paulista
dc.contributor.institution Kobe Gakuin Univ
dc.description.affiliation Universidade Federal de São Paulo, Dept Biophys, BR-04044020 São Paulo, Brazil
dc.description.affiliation Univ Estadual Paulista, Dept Biochem & Chem Technol, BR-14800900 São Paulo, Brazil
dc.description.affiliation Kobe Gakuin Univ, Fac Pharmaceut Sci, Kobe, Hyogo 6512180, Japan
dc.description.affiliationUnifesp Universidade Federal de São Paulo, Dept Biophys, BR-04044020 São Paulo, Brazil
dc.identifier.doi 10.1248/cpb.55.468
dc.description.source Web of Science
dc.identifier.wos WOS:000245935200025



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