Tryptophan-norleucine 1,5-disubstituted tetrazoles as cis peptide bond mimics: Investigation of the bioactive conformation of a potent and selective peptide for the cholecystokinin-B receptor

Lakmal W. Boteju; Teresa Zalewska; Henry I. Yamamura; Victor J. Hruby

doi:10.1016/S0960-894X(01)81005-2

Tryptophan-norleucine 1,5-disubstituted tetrazoles as cis peptide bond mimics: Investigation of the bioactive conformation of a potent and selective peptide for the cholecystokinin-B receptor

Lakmal W. Boteju, Teresa Zalewska, Henry I. Yamamura, Victor J. Hruby

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

10 Scopus citations

Abstract

It has been suggested that the cis conformation about the TrpNMeNle amide bond is important in conferring high affinity and selectivity to CCK-B receptor ligands. Substitution of the cis amide bond mimic Trpψ(CH₄)Nle into the peptide Gly-Trp-N-(Me)Nle-Asp-PheNH₂ causes it to lose activity, suggesting that other structural effects of N-(Me)Nle incorporation may be important for high affinity selectivity for the CCK-B receptor.

Original language	English (US)
Pages (from-to)	2011-2016
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	3
Issue number	10
DOIs	https://doi.org/10.1016/S0960-894X(01)81005-2
State	Published - Oct 1993
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(01)81005-2

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Tryptophan-norleucine 1,5-disubstituted tetrazoles as cis peptide bond mimics: Investigation of the bioactive conformation of a potent and selective peptide for the cholecystokinin-B receptor. / Boteju, Lakmal W.; Zalewska, Teresa; Yamamura, Henry I. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 3, No. 10, 10.1993, p. 2011-2016.

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

Boteju, LW, Zalewska, T, Yamamura, HI & Hruby, VJ 1993, 'Tryptophan-norleucine 1,5-disubstituted tetrazoles as cis peptide bond mimics: Investigation of the bioactive conformation of a potent and selective peptide for the cholecystokinin-B receptor', Bioorganic and Medicinal Chemistry Letters, vol. 3, no. 10, pp. 2011-2016. https://doi.org/10.1016/S0960-894X(01)81005-2

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Tryptophan-norleucine 1,5-disubstituted tetrazoles as cis peptide bond mimics: Investigation of the bioactive conformation of a potent and selective peptide for the cholecystokinin-B receptor

Abstract

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