Synthesis and some biological properties of 1-deamino-4-glu-oxytocin (1-beta-mercaptopropionic acid-4-glutamic acid-oxytocin) and its use in preparing a hormone-agarose complex.
1-Deamino-4-glu-oxytocin (1-beta-mercaptopropionic acid-4-glutamic acid - oxytocin) was synthesized by sequential reduction by sodium in liquid ammonia and oxidation by hydrogen peroxide of the octapeptide derivative, S-benzyl-beta-mercaptopropionyl-tyrosyl-isoleucyl-gamma-O-benzyl-glutamyl-asparaginyl-S-benzyl-cysteinyl-prolyl-leucyl-glycinamide. The oxidation analogue was isolated and purified by partition chromatography in two different solvent systems followed by exclusion chromatography on Sephadex G-25. It was found to possess approximately 13 I.U. of uterotonic activity, 34 I.U. of milk ejection activity, and 83 I.U. of milk ejection-like activity per milligram, measured on an isolated strip of lactating mouse mammary gland. 1-Deamino-4-Glu-oxytocin was coupled to AH-Sepharose 4B by the way of the free gamma-carboxyl group of its residue of glutamic acid. The water soluble 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride caused the coupling with approximately 70% effectiveness. The resultant peptide-agarose complex had low biological potency in the assay of milk ejection-like activity.
D000818:Animals; D001681:Biological Assay; D005260:Female; D005971:Glutamates; D007774:Lactation; D008321:Mammary Glands, Animal / Q000378:metabolism; D051379:Mice; D008892:Milk / Q000378:metabolism; D010121:Oxytocin / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000494:pharmacology; D011247:Pregnancy; D011485:Protein Binding; D011817:Rabbits; D012685:Sepharose; D013438:Sulfhydryl Compounds; D014599:Uterus / Q000187:drug effects
D005971:Glutamates; D013438:Sulfhydryl Compounds; D010121:Oxytocin; D012685:Sepharose