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Limiting Assumptions in the Design of Peptidomimetics
Department of Biochemistry and Molecular Biophysics, Washington University School of Medicine, St. Louis, Missouri 63110, United States..
Department of Biochemistry and Molecular Biophysics, Washington University School of Medicine, St. Louis, Missouri 63110, United States..ORCID iD: 0000-0002-4831-3423
2017 (English)In: Drug development research (Print), ISSN 0272-4391, E-ISSN 1098-2299, Vol. 78, no 6, 245-267 p.Article, review/survey (Refereed) Published
Abstract [en]

Limiting the flexibility of organic compounds to enhance their affinity and selectivity for targeting a macromolecule involved in molecular recognition has become a well-developed paradigm in medicinal chemistry. While the role of reverse-turn motifs as peptidomimetics has received the most attention, β-sheets and helices are also important motifs for protein/protein interactions. The more complicated problem of mimicking the interacting surface of noncontiguous epitopes will not be considered in this review. This limited overview focuses on efforts to use amino acid synthons as secondary-structure mimetics as well as providing examples of peptidomimetic design focused on nonpeptide synthetic chemistry in contrast. In particular, the rationale of optimal design criteria for mimicry and the many naïve violations of those criteria made in its pursuit are emphasized.

Place, publisher, year, edition, pages
2017. Vol. 78, no 6, 245-267 p.
Keyword [en]
peptidomimetics, beta-sheet mimetics, helix mimetics reverse-turn mimetics, semi-rigid analogs
National Category
Medicinal Chemistry Pharmaceutical Sciences Organic Chemistry Computer Science
Identifiers
URN: urn:nbn:se:uu:diva-328949DOI: 10.1002/ddr.21406OAI: oai:DiVA.org:uu-328949DiVA: diva2:1138616
Available from: 2017-09-06 Created: 2017-09-06 Last updated: 2017-09-07

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Publisher's full texthttp://onlinelibrary.wiley.com/doi/10.1002/ddr.21406/full

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