Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics

Wei Qiu; Xuyuan Gu; Vadim A. Soloshonok; Michael D. Carducci; Victor J. Hruby

doi:10.1016/S0040-4039(00)01864-5

Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics

Wei Qiu, Xuyuan Gu, Vadim A. Soloshonok, Michael D. Carducci, Victor J. Hruby

Chemistry and Biochemistry

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

85 Scopus citations

Abstract

Peptide side chains play critical roles in the event of molecular recognition. In order to study the bioactive conformation of parent peptides, a concise and straightforward five-step synthesis of [5.5]-bicyclic reverse turn dipeptide mimetic scaffolds with side chain functionality at the i + 1 and i + 2 positions has been developed. In the bicyclic structure, two dihedral angles (ψ₂ and φ₃) are greatly restricted.

Original language	English (US)
Pages (from-to)	145-148
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4039(00)01864-5
State	Published - Jan 8 2001

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)01864-5

Cite this

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title = "Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics",

abstract = "Peptide side chains play critical roles in the event of molecular recognition. In order to study the bioactive conformation of parent peptides, a concise and straightforward five-step synthesis of [5.5]-bicyclic reverse turn dipeptide mimetic scaffolds with side chain functionality at the i + 1 and i + 2 positions has been developed. In the bicyclic structure, two dihedral angles (ψ2 and φ3) are greatly restricted.",

author = "Wei Qiu and Xuyuan Gu and Soloshonok, {Vadim A.} and Carducci, {Michael D.} and Hruby, {Victor J.}",

note = "Funding Information: W.Q. would like to thank the following individuals for helpful discussions: Dr. Robert Bates, Mr. Jinfa Ying, and Dr. Neil Jacobsen (NMR); Dr. Richard Glass, Dr. Rodney L. Johnson, and Dr. John Rainier (synthesis); Dr. Guoxia Han (molecular modeling). Financial support for this work was provided by grants from the USPHS DK 17420, NIDA DA 06284 and DA 13449. The views expressed are those of the authors and are not necessarily those of the USPHS.",

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AU - Gu, Xuyuan

AU - Soloshonok, Vadim A.

AU - Carducci, Michael D.

AU - Hruby, Victor J.

N1 - Funding Information: W.Q. would like to thank the following individuals for helpful discussions: Dr. Robert Bates, Mr. Jinfa Ying, and Dr. Neil Jacobsen (NMR); Dr. Richard Glass, Dr. Rodney L. Johnson, and Dr. John Rainier (synthesis); Dr. Guoxia Han (molecular modeling). Financial support for this work was provided by grants from the USPHS DK 17420, NIDA DA 06284 and DA 13449. The views expressed are those of the authors and are not necessarily those of the USPHS.

PY - 2001/1/8

Y1 - 2001/1/8

N2 - Peptide side chains play critical roles in the event of molecular recognition. In order to study the bioactive conformation of parent peptides, a concise and straightforward five-step synthesis of [5.5]-bicyclic reverse turn dipeptide mimetic scaffolds with side chain functionality at the i + 1 and i + 2 positions has been developed. In the bicyclic structure, two dihedral angles (ψ2 and φ3) are greatly restricted.

AB - Peptide side chains play critical roles in the event of molecular recognition. In order to study the bioactive conformation of parent peptides, a concise and straightforward five-step synthesis of [5.5]-bicyclic reverse turn dipeptide mimetic scaffolds with side chain functionality at the i + 1 and i + 2 positions has been developed. In the bicyclic structure, two dihedral angles (ψ2 and φ3) are greatly restricted.

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Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics

Abstract

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CCDC 160341: Experimental Crystal Structure Determination

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Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 160341: Experimental Crystal Structure Determination

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