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

1992; Wiley; Volume: 39; Issue: 3 Linguagem: Inglês

10.1111/j.1399-3011.1992.tb00789.x

0367-8377

K. M. Sivanandaiah, Vommina V. Suresh Babu, CHANDRAMOWLY RENUKESHWAR,

Biochemical and Structural Characterization

Fmoc‐amino acid chlorides were employed in the solid phase synthesis of the opioid peptides [Leu]enkephalin, [Leu]enkephalin amide, and dermorphin. The conventional polystyrene‐based Merrifield resin or Wang's resin served as solid support. A binary salt of either triethylamine or diisopropylethylamine in the presence of 1‐hydroxybenzotriazole or pivalic acid was used for acylation. The coupling rates were quite fast, being comparatively faster when 1‐hydroxybenzotriazole was used along with triethylamine or diisopropylethylamine. The peptides obtained in good yields showed, after purification, biological and spectral properties identical with those of the natural peptides.