Formation of peptide thioamides by use of Fmoc amino monothioacids and PyBOP.
1991; Elsevier BV; Volume: 32; Issue: 51 Linguagem: Inglês
10.1016/0040-4039(91)80549-l
ISSN1873-3581
AutoresThomas Høeg-Jensen, Mogens Jakobsen, Carl Erik Olsen, Arne Holm,
Tópico(s)Organophosphorus compounds synthesis
ResumoEndothiopeptides have been obtained by using PyBOP® promoted coupling between Fmoc-protected amino monothioacids and amino acid or peptide esters. The protected endothiopeptides (Fmoc-Gly-ψ(CSNH)-Phe-OEt, Fmoc-Tyr(But)-ψ(CSNH)-Gly-Gly-Phe-Leu-OBut and Fmoc-Gln(Trt)-ψ(CSNH)-Phe-OEt) were formed (55, 45 and 37% yield) in admixture with the corresponding oxopeptides, from which they were easily separated chromatographically. Preliminary racemisation studies indicate that products of high optical purity are obtained. The mechanism for endothiopeptide formation is briefly discussed.
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