Synthesis of oxytocin using iodine for oxidative cyclization and silica gel adsorption chromatography for purification

Int J Pept Protein Res. 1979 Feb;13(2):137-41. doi: 10.1111/j.1399-3011.1979.tb01861.x.

Abstract

Oxytocin (OT) was synthesized employing the solid phase method. Resins made of copolymers of polystyrene-1%-crosslinked with divinylbenzene gave better yields (73-95%) of Z-Cys(Bzl)-Tyr(Bzl)-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-NH2 (I) than 2%-crosslinked resins (10--56%). Reduction of I with Na-liq.NH3 and oxidation with I2-MeOH at -40 degrees minimized dimer and polymer formation, and resulted in good yields (49--54%) of OT. The large volumes of MeOH required when several grams of I are reduced and then oxidized were rapidly evaporated in vacuo, and the residue was desalted by dissolving the peptide in a small volume of glacial acetic acid and filtering to remove the salt. OT was purified by adsorption chromatography on a silica gel column with combinations of MeOH-CHCl3 of graded polarity. Oxytocin elutes with 33% MeOH-CHCl3. After two purification steps by adsorption chromatography, the resulting OT was found to be homogeneous. The hormone was characterized chemically and found to be active biologically.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adsorption
  • Amino Acid Sequence
  • Chromatography, Gel
  • Cyclization
  • Iodine*
  • Oxidation-Reduction
  • Oxytocin / analysis
  • Oxytocin / chemical synthesis*

Substances

  • Oxytocin
  • Iodine