Synthesis of the isotopically labelled C-terminal fragment of zervamicin: An approach to the synthesis of Aib-containing peptides

Article abstract of DOI:10.1002/jlac.199719970109

The isotopically labelled C-terminal fragment of zervamicin, H-Hyp¹⁰-[4,4-²H₂-Gln]-Aib-Hyp-Aib-Pro-Phl ¹⁶, has been synthesized in solution by a Fmoc/tert-butyl strategy in 28% overall yield. The Fmoc group was removed by reaction for 2 min with 0.1 M NaOH in dioxane/methanol/water, (30:9:1, v:v:v). The couplings of the sterically hindered Aib residues were achieved by means of either BOP/DMAP activation or Fmoc-Aib-Cl. Acid deprotection of the peptide was performed by reaction with 50% TFA in CH₂Cl₂ for 30 min without significant cleavage of the acid-labile Aib-Pro and Aib-Hyp peptide bonds. VCH Verlagsgcsellschaft mbH, 1997.