Application of gel-phase 19F NMR spectroscopy for optimization of solid-phase synthesis of a hydrophobic peptide from the signal sequence of the mucin MUC1
2007 (English)In: Journal of Peptide Science, ISSN 1075-2617, Vol. 13, no 5, 354-361 p.Article in journal (Refereed) Published
This paper describes the manual Fmoc/t-Bu solid-phase synthesis of a difficult nine-residue hydrophobic peptide LLLLTVLTV from one of the signal sequences that flank the tandem repeat of the mucin MUC1. Gel-phase 19F NMR spectroscopy was used as a straightforward method for optimization of the solid-phase synthesis. Different approaches were applied for comparative studies. The strategy based on modified solid-phase conditions using DIC/HOAt for coupling, DBU for Fmoc deprotection, and the incorporation of the pseudo proline dipeptide Fmoc-Leu-Thr(Me, Me pro)-OH as a backbone-protecting group was found to be superior according to gel-phase 19F NMR spectroscopy. Implementation of the optimized Fmoc protocol enabled an effective synthesis of signal peptide LLLLTVLTV.
Place, publisher, year, edition, pages
2007. Vol. 13, no 5, 354-361 p.
solid-phase peptide synthesis, difficult sequence, gel-phase 19F NMR, pseudo proline
IdentifiersURN: urn:nbn:se:umu:diva-12721DOI: doi:10.1002/psc.850OAI: oai:DiVA.org:umu-12721DiVA: diva2:152392