Studies on Peptides. XVI. Regeneration of Lysine from Nε-Formyllysine by Aqueous Hydrazine or Hydroxylamine and Their Application to the Synthesis of α-Melanocyte-stimulating Hormone

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Abstract
Treatment of Nε-formyllysine with dilute aqueous hydrazine acetate or hydroxylamine hydrochloride in aqueous pyridine regenerated lysine in satisfactory yield. These methods were adopted to convert Nα-acetylseryltyrosylserylmethionylglutamylhistidylphenyl-alanylarginyltryptophylglycyl-Nε-formyllysylprolylvaline amide to α-melanocyte-stimulating hormone (MSH). The products prepared by two alternate methods behaved quite identically with natural α-MSH on paper and thin-layer chromatographies and their infrared spectra were both identical with that of natural α-MSH. Their in vitro MSH activities were 2.3-5.4×1012 and 2.4-4.1×1012 U/g respectively.