Fmoc-POAC: [(9-fluorenylmethyloxycarbonyl)-2,2,5,5-tetramethylpyrrolidine-N-oxyl-3-amino-4-carboxylic acid]: A novel protected spin labeled beta-amino acid for peptide and protein chemistry

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dc.contributor.authorTominaga, M.
dc.contributor.authorBarbosa, SR
dc.contributor.authorPoletti, E. F.
dc.contributor.authorZukerman-Schpector, J.
dc.contributor.authorMarchetto, Reinaldo [UNESP]
dc.contributor.authorSchreier, S.
dc.contributor.authorPaiva, ACMM
dc.contributor.authorNakaie, C. R.
dc.contributor.institutionUniversidade Federal de São Paulo (UNIFESP)
dc.contributor.institutionUniversidade Federal de São Carlos (UFSCar)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2014-05-20T15:28:41Z
dc.date.available2014-05-20T15:28:41Z
dc.date.issued2001-08-01
dc.description.abstractThe stable free radical 2,2,6,6-tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic acid (TOAC) is the only spin labeled amino acid that has been used to date to successfully label peptide sequences for structural studies. However, severe difficulty in coupling the subsequent amino acid has been the most serious shortcoming of this paramagnetic marker. This problem stems from the low nucleophilicity of TOAC's amine group towards the acylation reaction during peptide chain elongation. The present report introduces the alternative beta -amino acid 2,2,5,5-tetramethylpyrrolidine-N-oxyl-3-amino-4-carboxylic acid (POAC), potentially useful in peptide and protein chemistry. Investigations aimed at addressing the stereochemistry of this cyclic molecule through X-ray diffraction measurements of crystalline and bulk samples revealed that it consists only of the trans conformer. The 9-fluorenylmethyloxyearbonyl group (Fmoc) was chosen for temporary protection of the POAC amine function, allowing insertion of the probe at any position in a peptide sequence. The vasoactive octapeptide angiotensin II (AII, DRVYIHPF) was synthesized by replacing Pro(7) with POAC. The reaction of Fmoc-POAC with the peptidyl-resin occurred smoothly, and the coupling of the subsequent amino acid showed a much faster reaction when compared with TOAC. POAC(7)-AII was obtained in good yield, demonstrating that, in addition to TOAC, POAC is a convenient amino acid for the synthesis of spin labeled peptide analogues. The present findings open the possibility of a wide range of chemical and biological applications for this novel beta -amino acid derivative, including structural investigations involving its differentiated bend-inducing characteristics.en
dc.description.affiliationUniv Fed São Paulo, Dept Biophys, BR-04044020 São Paulo, Brazil
dc.description.affiliationUniv Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil
dc.description.affiliationUNESP, Inst Chem, Dept Biochem, BR-14800060 Araraquara, SP, Brazil
dc.description.affiliationUniv São Paulo, Inst Chem, Dept Biochem, BR-05513970 São Paulo, Brazil
dc.description.affiliationUnespUNESP, Inst Chem, Dept Biochem, BR-14800060 Araraquara, SP, Brazil
dc.format.extent1027-1029
dc.identifierhttp://dx.doi.org/10.1248/cpb.49.1027
dc.identifier.citationChemical & Pharmaceutical Bulletin. Tokyo: Pharmaceutical Soc Japan, v. 49, n. 8, p. 1027-1029, 2001.
dc.identifier.doi10.1248/cpb.49.1027
dc.identifier.fileWOS000170110400018.pdf
dc.identifier.issn0009-2363
dc.identifier.lattes5711182251641103
dc.identifier.urihttp://hdl.handle.net/11449/38440
dc.identifier.wosWOS:000170110400018
dc.language.isoeng
dc.publisherPharmaceutical Soc Japan
dc.relation.ispartofChemical & Pharmaceutical Bulletin
dc.relation.ispartofjcr1.258
dc.relation.ispartofsjr0,364
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectpeptidept
dc.subjectspin labelpt
dc.subjectelectron paramagnetic resonancept
dc.subjectamino acidpt
dc.subjectTOACpt
dc.subjectPOACpt
dc.titleFmoc-POAC: [(9-fluorenylmethyloxycarbonyl)-2,2,5,5-tetramethylpyrrolidine-N-oxyl-3-amino-4-carboxylic acid]: A novel protected spin labeled beta-amino acid for peptide and protein chemistryen
dc.typeArtigo
dcterms.licensehttp://bpb.pharm.or.jp/document/transfer.pdf
dcterms.rightsHolderPharmaceutical Soc Japan
unesp.author.lattes5711182251641103
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Química, Araraquarapt

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