title: Solid phase synthesis of apamin, the principal neurotoxin in bee venom. Isolation and characterization of acetamidomethyl apamin.
abstract: The synthesis of apamin, the principal neurotoxin in bee venom, has been accomplished by the solid phase method on a benzhydrylamine resin, 2-Phenylisopropyloxycarbonyl amino acids were used throughout the synthesis except for the C-terminal histidine. Improved yields in the coupling steps in the N-terminal part of the molecule were obtained by coupling each amino acid both in dichloromethane and dimethylformamide. The use of acetamidomethyl as an S-protecting group for cysteine made it possible to isolate and purify the linear peptide. The deblocked and oxidized peptide was fractionated by ion-exchange chromatography (Bio-Rex 70) to obtain a highly purified apamin with full biological activity and with the same physical and chemical properties as the natural peptide. Circular dichroism (CD) spectra of the synthetic and natural apamin were identical.
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D001030:Apamin / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000633:toxicity; D001514:Bee Venoms / Q000138:chemical synthesis*; D002852:Chromatography, Ion Exchange; D002942:Circular Dichroism; D051379:Mice; D009498:Neurotoxins / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000633:toxicity; D010084:Oxidation-Reduction; D012116:Resins, Plant
chemical_list: D001514:Bee Venoms; D009498:Neurotoxins; D012116:Resins, Plant; D001030:Apamin