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Cyclic Aromatic Amino Acids with Constrained χ1 and χ2 Dihedral Angles

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Peptidomimetics Protocols

Part of the book series: Methods in Molecular Medicine™ ((MIMM,volume 23))

Abstract

The concept of topographic design of peptide neurotransmitters and hormones was pioneered by Hruby (1,2). When the design involved primarily constraint of the side chains of a peptide that has a well-defined backbone conformation, the term “topographic design on a stable template” was proposed (3). The side chain χ1 of aromatic amino acids, such as Phe, Trp, Tyr, and His, can be constrained in either the gauche (−) or gauche (+) conformation by linking the nitrogen atom to the aromatic ring through a methylene bridge (Fig. 1).

Principle of side-chain constraint for Phe, Trp, and His.

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Author information

Authors and Affiliations

  1. Organic Chemistry Department, Vrije Universiteit Brussel, Brussels, Belgium

    Dirk Tourwé & Koen Iterbeke

  2. Department of Medicinal Chemistry, Glaxo Wellcome Research and Development, Research Triangle Park, NC

    Wieslaw M. Kazmierski

  3. Isotope Laboratory, Biological Research Centre, Hungarian Academy of Sciences, Szeged, Hungary

    Géza Tóth

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  1. Dirk Tourwé
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  2. Koen Iterbeke
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  3. Wieslaw M. Kazmierski
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  4. Géza Tóth
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Editors and Affiliations

  1. Glaxo Wellcome., Inc., Research Triangle Park, NC

    Wieslaw M. Kazmierski

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© 1999 Humana Press Inc., Totowa, NJ

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Tourwé, D., Iterbeke, K., Kazmierski, W.M., Tóth, G. (1999). Cyclic Aromatic Amino Acids with Constrained χ1 and χ2 Dihedral Angles. In: Kazmierski, W.M. (eds) Peptidomimetics Protocols. Methods in Molecular Medicine™, vol 23. Humana Press. https://doi.org/10.1385/0-89603-517-4:321

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  • DOI: https://doi.org/10.1385/0-89603-517-4:321

  • Publisher Name: Humana Press

  • Print ISBN: 978-0-89603-517-1

  • Online ISBN: 978-1-59259-605-8

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