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Prediction of difficult sequences in solid-phase peptide synthesis


Deprotection peak profiles have been determined as a measure of internal aggregation during Fmoc-polyahttp://www.peptidetj.com/news/custom-peptide-synthesis-7.htmlmide continuous flow solid phase synthesis. The results have been correlated with amino-acid structure and discussed in terms of minimising aggregation during synthesis.
The phenomenon of a difficult sequencea has long frustrated chemists in their efforts to assemble peptides that contain such sequences by solid phase synthesis methods. A variety of remedial measures are available to minimize or even abolish the negative impact of these sequences during synthesis. These include the use of elevated temperatures and stronger acylating reagents. Amyloid-?2, a fragment of the amyloid precursor protein, contains 40-43 residues and possesses a C-terminal sequence that is particularly resistant to ready solid phase synthesis making it a a difficult sequencea peptide. This review focuses on approaches to successfully assemble the peptide by both Boc- and Fmoc solid phase synthesis.
The common mechanistic origin of the phenomena of segment insolubility in solution-phase and sequence-related incomplete aminoacylations in solid-phase custom peptide synthesis is used as the basis of a model for difficult sequences in which partial .beta.-sheet hydrogen bonding by the pendant peptide chains of the peptidoresin is the dominant causative principle. A predictive method based on optimized Chou and Fasman type coil conformational parameters is proposed for the identification of such difficult sequences and is tested by its successful application to 101 previously performed solid-phase custom peptide synthesis (986 aminoacylation reactions). The use of optimized chemical tactics, secondary structure disruption reagents and tertiary amide linkages between amino acid residues is discussed with a view to improving the solid-phase synthesis of peptides containing difficult sequences.
custom peptide synthesis
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