Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors

Junyi Zhang; Chiyi Xiong; Jinfa Ying; Wei Wang; Victor J. Hruby

doi:10.1021/ol0351347

Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors

Junyi Zhang, Chiyi Xiong, Jinfa Ying, Wei Wang, Victor J. Hruby

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

(Matrix presented) The novel dipeptide β-turn mimetic, 4,8-disubstituted azabicyclo[4.3.0]nonane amino acid ester (15), has been synthesized to serve as a peptide mimetic of the dipeptide Phe-Arg, which contains two important pharmacophore elements in melanotropin peptides. Introduction of side-chain functionality at C-8 was achieved by using β-functionalized pyroglutamate (8) as a synthetic precursor. The side chain at C-4 was introduced by bromination of dehydroamino acid intermediate (10) followed by Suzuki cross-coupling.

Original language	English (US)
Pages (from-to)	3115-3118
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	17
DOIs	https://doi.org/10.1021/ol0351347
State	Published - Aug 21 2003

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors",

abstract = "(Matrix presented) The novel dipeptide β-turn mimetic, 4,8-disubstituted azabicyclo[4.3.0]nonane amino acid ester (15), has been synthesized to serve as a peptide mimetic of the dipeptide Phe-Arg, which contains two important pharmacophore elements in melanotropin peptides. Introduction of side-chain functionality at C-8 was achieved by using β-functionalized pyroglutamate (8) as a synthetic precursor. The side chain at C-4 was introduced by bromination of dehydroamino acid intermediate (10) followed by Suzuki cross-coupling.",

author = "Junyi Zhang and Chiyi Xiong and Jinfa Ying and Wei Wang and Hruby, {Victor J.}",

year = "2003",

month = aug,

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doi = "10.1021/ol0351347",

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T1 - Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors

AU - Zhang, Junyi

AU - Xiong, Chiyi

AU - Ying, Jinfa

AU - Wang, Wei

AU - Hruby, Victor J.

PY - 2003/8/21

Y1 - 2003/8/21

N2 - (Matrix presented) The novel dipeptide β-turn mimetic, 4,8-disubstituted azabicyclo[4.3.0]nonane amino acid ester (15), has been synthesized to serve as a peptide mimetic of the dipeptide Phe-Arg, which contains two important pharmacophore elements in melanotropin peptides. Introduction of side-chain functionality at C-8 was achieved by using β-functionalized pyroglutamate (8) as a synthetic precursor. The side chain at C-4 was introduced by bromination of dehydroamino acid intermediate (10) followed by Suzuki cross-coupling.

AB - (Matrix presented) The novel dipeptide β-turn mimetic, 4,8-disubstituted azabicyclo[4.3.0]nonane amino acid ester (15), has been synthesized to serve as a peptide mimetic of the dipeptide Phe-Arg, which contains two important pharmacophore elements in melanotropin peptides. Introduction of side-chain functionality at C-8 was achieved by using β-functionalized pyroglutamate (8) as a synthetic precursor. The side chain at C-4 was introduced by bromination of dehydroamino acid intermediate (10) followed by Suzuki cross-coupling.

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Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors

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