Solid-phase peptide synthesis at elevated temperatures: a search for an optimized synthesis condition of unsulfated cholecystokinin-12

Solid-phase peptide synthesis at elevated temperatures: a search for an optimized synthesis condition of unsulfated cholecystokinin-12

Autor Varanda, Leandro M. Google Scholar
Miranda, M Teresa M Google Scholar
Instituição Universidade Federal de São Paulo (UNIFESP)
Resumo A systematic investigation of solid-phase peptide synthesis at elevated temperatures using the well-known aggregating peptide acyl carrier protein (65-74) and the unsulfated cholecystokinin-8 as models is presented. The main goal of the investigation was the determination of an optimized experimental condition for the synthesis of unsulfated cholecystokinin-12. Of the elevated temperatures used, 60 degrees C was the most appropriate. The efficiency of N,N'-diisopropylcarbodiimide/1-hydroxybenzotriazole (DIG/HOBt) in 25% dimethyl sulfoxide (DMSO)/toluene at this temperature was similar to that of 2-(1-H-benzotriazole-1-yl)-1.1.3.3-tetramethyluronium tetrafluoroborate (TBTU). Interestingly, this coupling reagent was more efficient than TB?ZI, benzotriazol-1-yl oxytris(dimethylamino)phosphonium and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate in N-methylpyrrolidone. 25%DMSO/toluene proved to be suitable for the swelling of the resins phenylacetamidomethyl, methylbenzhydrylamine, hydroxymethylphenoxy, 4-(benzyloxy)-2',4'-dimethoxybenzhydrylamine, 4-(2',3'dimethoxyphenyl-Fmoc-aminomethyl) ??phenoxy and (4-succinylamido-2',2',4'-trimethoxy)benzhydrylamine. Those polymeric supports were fully compatible with the approach. Under the optimized synthesis condition found in these studies (temperature of 60 degrees C, DIC/HOBt as coupling reagent and 25% DMSO/toluene as solvent), no difficulties related to the aggregation phenomenon were encountered. These data confirm the usefulness of solid-phase peptide synthesis at elevated temperatures and extend its applicability. (C) Munksgaard 1997.
Assunto elevated temperature
peptide
synthesis
Idioma Inglês
Data 1997-08-01
Publicado em Journal Of Peptide Research. Copenhagen: Munksgaard Int Publ Ltd, v. 50, n. 2, p. 102-108, 1997.
ISSN 1397-002X (Sherpa/Romeo, fator de impacto)
Editor Munksgaard Int Publ Ltd
Extensão 102-108
Fonte http://dx.doi.org/10.1111/j.1399-3011.1997.tb01175.x
Direito de acesso Acesso restrito
Tipo Artigo
Web of Science WOS:A1997XQ79600004
URI http://repositorio.unifesp.br/11600/44560

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