Firuz Shakoori, Archana Gangakhedkar
Oct 1, 2014
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Journal
Cancer Research
Abstract
Proceedings: AACR Annual Meeting 2014; April 5-9, 2014; San Diego, CA Hydrophobic peptides are common to be used in cancer vaccinations. Hydrophobic peptides, continue to present challenges for large scale production in peptide industry. Experimental Procedures: Full sequence prepared by Solid phase Synthesis:The peptide was synthesized with Fmoc-Lys(Boc)-Wang resin by using standard Fmoc/tBu chemistry. Protecting groups used for amino acids are: tBu for Thr, Boc for Trp and Lys and Boc-Ser- OH was used as a hydrolysis-labile ester provider. Fmoc-Leu-OH was coupled on the side chain of Ser by DIC/DMAP (Amino acid/DIC/DMAP, 3/1.5/0.3 eq). The other amino acids were assembled by repetitive removal of the Fmoc protecting group by treating with 2% DBU/2% piperidine in DMF 30 minutes and coupling of protected amino acid by using DIC/HOBt/NMM (4:4:4 eq) in 180 minutes to overnight. Ninhydrin test was performed after each coupling to check the coupling efficiency. After the last coupling,resin was washed and dried, then treated with reagent K for cleavage and removal of the side chain protecting groups. Crude peptide was precipitated from cold ether and collected by filtration. Table.1 Summary of 4 synthesize results View this table: Conclusion: American Peptide demonstrated the utility of a hydrophilic peptide ‘tail’ in purification of a hydrophobic peptide on both small (20-30 mmol) research scale and large (800 mmol) cGMP scales to provide the peptide in hundreds-of-grams quantities. The approach described allowed for both time-and cost-competitive manufacturing of this difficult peptide for clinical trials. Citation Format: Firuz Shakoori, Archana Gangakhedkar. Polylysine linker for successful manufacturing of hydrophobic peptides. [abstract]. In: Proceedings of the 105th Annual Meeting of the American Association for Cancer Research; 2014 Apr 5-9; San Diego, CA. Philadelphia (PA): AACR; Cancer Res 2014;74(19 Suppl):Abstract nr 4588. doi:10.1158/1538-7445.AM2014-4588