| Title: | Amino monothio acids in solid-phase synthesis of peptide thioamides |
| Author(s): | Hoeg-Jensen T; Spatola AF; Holm A; |
| Address: | "Chemistry Department, Royal Veterinary and Agricultural University, Frederiksberg, Denmark" |
| DOI: | 10.1111/j.1399-3011.1996.tb01344.x |
| ISSN/ISBN: | 0367-8377 (Print) 0367-8377 (Linking) |
| Abstract: | "Peptides containing backbone thioamides (endothiopeptides) have been synthesized utilizing thioacylation under solid-phase conditions. The thioacylations were performed by activating N-protected amino monothio acids with the phosphorus-containing coupling reagent 6-nitrobenzotriazol-l-yloxytris(pyrrolidino)phosphoniu m hexafluorophosphate (PyNOP). This method avoids the use of P4S10-based O/S-exchange reagents, and it is thus amendable to amino acids with side-chain amides. Synthesis of endothio analogs of biologically active peptide such a pGlu-psi [CSNH]-His-Pro-NH2 (TRH) and Leu-Gln-psi [CSNH]-Leu-Lys demonstrated this feature. Proton and carbon NMR spectra of the TRH analog verified the sequential position of its thioamide function. Compatibility of endothiopeptides with allylprotecting groups was studied, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was evaluated as a substitute for piperidine" |
| Keywords: | "Acylation Amino Acids/chemistry Chromatography, High Pressure Liquid Endothelins/antagonists & inhibitors Fluorenes/chemistry Magnetic Resonance Spectroscopy Mass Spectrometry Mating Factor Oligopeptides/*chemical synthesis/chemistry Peptides/chemistry Pe;" |
| Notes: | "MedlineHoeg-Jensen, T Spatola, A F Holm, A eng Denmark 1996/03/01 Int J Pept Protein Res. 1996 Mar; 47(3):190-200. doi: 10.1111/j.1399-3011.1996.tb01344.x" |
