2006
DOI: 10.1007/s10822-006-9059-x
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Do benzodiazepines mimic reverse-turn structures?

Abstract: The role of benzodiazepine derivatives (BZD) as a privileged scaffold that mimics beta-turn structures (Ripka et al. (1993) Tetrahedron 49:3593-3608) in peptide/protein recognition was reexamined in detail. Stable BZD ring conformers were determined with MM3, and experimental reverse-turn structures were extracted from the basis set of protein crystal structures previously defined by Ripka et al. Ideal beta-turns were also modeled and similarly compared with BZD conformers. Huge numbers of conformers were gene… Show more

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Cited by 29 publications
(27 citation statements)
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“…This small size correlates well with the dimensions of a β‐turn structure. The distance between the α‐carbon of residue i and the α‐carbon of residue i +3 has been determined experimentally to be between 4–6 Å in various naturally occurring reverse turn structures 19. Therefore, due to their small compact structure these rhenium diethylenetriamine metal constructs are of an appropriate scale to have application in the targeting of receptors that bind biologically active molecules in a turn conformation.…”
Section: Resultsmentioning
confidence: 99%
“…This small size correlates well with the dimensions of a β‐turn structure. The distance between the α‐carbon of residue i and the α‐carbon of residue i +3 has been determined experimentally to be between 4–6 Å in various naturally occurring reverse turn structures 19. Therefore, due to their small compact structure these rhenium diethylenetriamine metal constructs are of an appropriate scale to have application in the targeting of receptors that bind biologically active molecules in a turn conformation.…”
Section: Resultsmentioning
confidence: 99%
“…It has no reactive sites that might lead to instability or toxicity, and would be predicted to have good bioavailability. The structure of CHCP2 utilizes a benzodiazepine scaffold, considered one of the “privileged scaffolds” for biologically active compounds 16 .…”
Section: Discussionmentioning
confidence: 99%
“…[75] As a consequence of the two distinct conformations of its central seven-membered ring, the scaffold can be used to mimic almost all β-turn types. [76] Glucose is another scaffold ( 3 , Figure 4) that has been used to mimic β-turns, with a focus on mimicking the cyclic peptide somatostatin. [77] Notably, tetrahydropyrane-based β-turn mimetics were included in peptide sequences to serve as PPI inhibitors.…”
Section: Methodsmentioning
confidence: 99%