Fmoc‐amino acid chlorides in solid phase synthesis of opioid peptides

Abstract

Fmoc-amino acid chlorides were employed in the solid phase synthesis of the opioid peptides [Leulenkephalin. [ Leulenkephalin amide, and derniorphin. The conventional polystyrene-based Merrifield resin or Wang's resin served as solid support. A binary salt of either triethylaniine or diisopropylethylamine in the presence of I-hydroxybenzotriazole or pivalic acid was used for acylation. The coupling rates were quite fast, being comparatively faster when 1-hydroxybenzotriazole was used along with triethylaniine or diisopropylethylamine. The peptides obtained in good yields showed, after purification, biological and spectral properties identical with those of the natural peptides.Keil iwrh: amino acid chlorides: binary salt; coupling rate; ((9-fluoreny1methyl)oxy)carbonyl-amino acids: 1 -hydroxybenzotriazole: solid phase peptide synthesis

Fast Solution-Phase and Liquid-Phase Peptide Syntheses (SolPSS and LPPS) Mediated by Biomimetic Cyclic Propylphosphonic Anhydride (T3P®)

“…Based on the previous information, the protocol was applied to the synthesis of Leu-Enkephalin (H-Tyr-Gly-Gly-Phe-Leu-OH), a pentapeptide that has been commonly prepared to test the efficacy of a methodology in comparison with other synthetic techniques [29].…”