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 journalArticle

8 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2011-2016
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume3
Issue number10
DOIs
StatePublished - 1993

Fingerprint

Tetrazoles
Norleucine
Cholecystokinin B Receptor
Amides
Tryptophan
glycyltryptophan
Conformations
Peptides
Substitution reactions
Ligands
peptide B

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

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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.",
author = "Boteju, {Lakmal W.} and Teresa Zalewska and Yamamura, {Henry I.} and Hruby, {Victor J}",
year = "1993",
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T1 - Tryptophan-norleucine 1,5-disubstituted tetrazoles as cis peptide bond mimics

T2 - Investigation of the bioactive conformation of a potent and selective peptide for the cholecystokinin-B receptor

AU - Boteju, Lakmal W.

AU - Zalewska, Teresa

AU - Yamamura, Henry I.

AU - Hruby, Victor J

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

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U2 - 10.1016/S0960-894X(01)81005-2

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

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EP - 2016

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JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 10

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