Convergent Synthesis of Thioether Containing Peptides

Molecules

Christina Katakalou¹  Kleomenis Barlos¹  Dimitrios Gatos¹  Spyridon Mourtas¹ 

[1] Department of Chemistry, University of Patras, 26510 Rio Patras, Greece;

关键词: haloacylated peptides;    aminothiols;    bis(aminoalkyl)dithiols;    convergent solid phase peptide synthesis;    trityl-type resins;   

DOI  :  10.3390/molecules25010218

来源: DOAJ

【 摘 要 】

Thioether containing peptides were obtained following three synthetic routes. In route A, halo acids esterified on 2-chlorotrityl(Cltr) resin were reacted with N-fluorenylmethoxycarbonyl (Fmoc) aminothiols. These were either cleaved from the resin to the corresponding (Fmoc-aminothiol)carboxylic acids, which were used as key building blocks in solid phase peptide synthesis (SPPS), or the N-Fmoc group was deprotected and peptide chains were elongated by standard SPPS. The obtained N-Fmoc protected thioether containing peptides were then condensed either in solution, or on solid support, with the appropriate amino components of peptides. In route B, the thioether containing peptides were obtained by the reaction of N-Fmoc aminothiols with bromoacetylated peptides, which were synthesized on Cltr-resin, followed by removal of the N-Fmoc group and subsequent peptide elongation by standard SPPS. In route C, the thioether containing peptides were obtained by the condensation of a haloacylated peptide synthesized on Cltr-resin and a thiol-peptide synthesized either on 4-methoxytrityl(Mmt) or trityl(Trt) resin.

【 授权许可】

Unknown