Synthesis of 3β-acetoxy-17β-(l-arginyl-l-arginyl-l-prolyl)amino-5α-androstane

George Pettit, Robert L. Smith, H. Klinger

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Abstract

A steroidal peptide based on the 17-19 unit sequence of β-corticotropin has been synthesized. Construction of the title substance (tripeptide IIIe) was achieved starting from 3β-hydroxy-17β-amino-5α-androstane. The phenylisoxazolium method was used for peptide bond formation and a combination of acetyl (for the steroid nucleus), carbobenzoxy, and nitro (for arginine) protecting groups were employed. Peptide IIIe was characterized as the triacetate derivative and the assigned structure received additional support from results of an amino acid analysis.

Original languageEnglish (US)
Pages (from-to)145-148
Number of pages4
JournalJournal of Medicinal Chemistry
Volume10
Issue number2
Publication statusPublished - 1967

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ASJC Scopus subject areas

  • Organic Chemistry

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