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

George Pettit, Robert L. Smith, H. Klinger

Research output: Contribution to journalArticle

13 Citations (Scopus)

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
StatePublished - 1967

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Peptides
Adrenocorticotropic Hormone
Arginine
Steroids
Derivatives
Amino Acids
androstane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 3β-acetoxy-17β-(l-arginyl-l-arginyl-l-prolyl)amino-5α-androstane. / Pettit, George; Smith, Robert L.; Klinger, H.

In: Journal of Medicinal Chemistry, Vol. 10, No. 2, 1967, p. 145-148.

Research output: Contribution to journalArticle

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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.",
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