Synthesis of 3β-Acetoxy-17β-(L-Arginyl-L-Arginyl-L-Prolyl)Amino-5α-Androstane

George Pettit; Robert L. Smith; H. Klinger

doi:10.1021/jm00314a003

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 journal › Article › peer-review

13 Scopus citations

Abstract

A steroidal peptide based on the 17-19 unit sequence of β-corticotropin has been synthesized. Construction of the title substance (tripeptide Hie) 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 language	English (US)
Pages (from-to)	145-148
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	10
Issue number	2
DOIs	https://doi.org/10.1021/jm00314a003
State	Published - 1967

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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title = "Synthesis of 3β-Acetoxy-17β-(L-Arginyl-L-Arginyl-L-Prolyl)Amino-5α-Androstane",

abstract = "A steroidal peptide based on the 17-19 unit sequence of β-corticotropin has been synthesized. Construction of the title substance (tripeptide Hie) 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.",

author = "George Pettit and Smith, {Robert L.} and H. Klinger",

year = "1967",

doi = "10.1021/jm00314a003",

language = "English (US)",

volume = "10",

pages = "145--148",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "2",

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TY - JOUR

T1 - Synthesis of 3β-Acetoxy-17β-(L-Arginyl-L-Arginyl-L-Prolyl)Amino-5α-Androstane

AU - Pettit, George

AU - Smith, Robert L.

AU - Klinger, H.

PY - 1967

Y1 - 1967

N2 - A steroidal peptide based on the 17-19 unit sequence of β-corticotropin has been synthesized. Construction of the title substance (tripeptide Hie) 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.

AB - A steroidal peptide based on the 17-19 unit sequence of β-corticotropin has been synthesized. Construction of the title substance (tripeptide Hie) 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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DO - 10.1021/jm00314a003

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SP - 145

EP - 148

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 2

ER -

Synthesis of 3β-Acetoxy-17β-(L-Arginyl-L-Arginyl-L-Prolyl)Amino-5α-Androstane

Abstract

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