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

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

46 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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10.1021/ol0351347

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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,

day = "21",

doi = "10.1021/ol0351347",

language = "English (US)",

volume = "5",

pages = "3115--3118",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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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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JO - Organic Letters

JF - Organic Letters

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ER -

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

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CCDC 219371: Experimental Crystal Structure Determination

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

Abstract

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CCDC 219371: Experimental Crystal Structure Determination

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