Fmoc-amino acid chlorides in solid phase synthesis of opioid peptides.
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.
Sivanandaiah
K M
KM
Department of Studies in Chemistry, Central College, Bangalore University, India.
Babu
V V
VV
Renukeshwar
C
C
D000215:Acylation; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004743:Enkephalin, Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005021:Ethylamines; D005449:Fluorenes / Q000737:chemistry*; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D018847:Opioid Peptides; D014230:Triazoles
D000596:Amino Acids; D002712:Chlorides; D005021:Ethylamines; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D009842:Oligopeptides; D018847:Opioid Peptides; D014230:Triazoles; C030058:dermorphin; D004743:Enkephalin, Leucine; C027070:N,N-diisopropylethylamine; C048614:enkephalinamide-Leu; C011852:1-hydroxybenzotriazole; C016162:triethylamine