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Special Issue "Peptidomimetics"

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A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Molecular Recognition".

Deadline for manuscript submissions: closed (15 December 2010)

Special Issue Editor

Guest Editor
Prof. Dr. Peter Huber

Radiation Oncology, German Cancer Research Center (dkfz), 280 INF, Heidelberg 69120, Germany

Keywords

  • peptidomimetics

Published Papers (1 paper)

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Review

Open AccessReview Conformationally Constrained Histidines in the Design of Peptidomimetics: Strategies for the χ-Space Control
Int. J. Mol. Sci. 2011, 12(5), 2853-2890; doi:10.3390/ijms12052853
Received: 31 March 2011 / Revised: 18 April 2011 / Accepted: 20 April 2011 / Published: 3 May 2011
Cited by 10 | PDF Full-text (545 KB) | HTML Full-text | XML Full-text
Abstract
A successful design of peptidomimetics must come to terms with χ-space control. The incorporation of χ-space constrained amino acids into bioactive peptides renders the χ1 and χ2 torsional angles of pharmacophore amino acids critical for activity and selectivity as with [...] Read more.
A successful design of peptidomimetics must come to terms with χ-space control. The incorporation of χ-space constrained amino acids into bioactive peptides renders the χ1 and χ2 torsional angles of pharmacophore amino acids critical for activity and selectivity as with other relevant structural features of the template. This review describes histidine analogues characterized by replacement of native α and/or β-hydrogen atoms with alkyl substituents as well as analogues with α, β-didehydro unsaturation or Cα-Cβ cyclopropane insertion (ACC derivatives). Attention is also dedicated to the relevant field of β-aminoacid chemistry by describing the synthesis of β2- and β3-models (β-hHis). Structural modifications leading to cyclic imino derivatives such as spinacine, aza-histidine and analogues with shortening or elongation of the native side chain (nor-histidine and homo-histidine, respectively) are also described. Examples of the use of the described analogues to replace native histidine in bioactive peptides are also given. Full article
(This article belongs to the Special Issue Peptidomimetics)

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