Synthesis and solid-phase application of suitably protected gamma-hydroxyvaline building blocks.

ABSTRACT: Recently, an unexpected modified residue, gamma-hydroxy-D-valine (D-Hyv), was identified within ribosomally expressed polypeptide chains of four conopeptides from the venoms of Conus gladiator and Conus mus. To assemble Hyv-containing peptides, we have explored several routes for the synthesis of appropriately functionalized Hyv building blocks. D-Hyv was produced from D-Val by using a variation of the previously published K2PtCl4/CuCl2 oxidative method. Direct synthesis of Boc- or Cbz-D-Hyv lactone proceeded in low yield; additionally, the lactones are too unreactive for solid-phase applications. 9-Borabicyclononane or copper-complexed D-Hyv was prepared and treated with tert-butyldimethylsilyl trifluoromethanesulfonate (TBDMSOTf) to produce D-Hyv(O-TBDMS). The most efficient complex disr

SUBMITTER: Cudic M 

PROVIDER: S-EPMC2551766 | biostudies-literature | 2007 Jul

REPOSITORIES: biostudies-literature