Aromatic δ-Peptides

Jiang, Hua; Léger, Jean‐Michel; Huc, Ivan

doi:10.1021/ja029887k

Cited by 290 publications

(174 citation statements)

References 8 publications

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“…The quinoline (Q) trimers at each extremity of the strand are known to code for a strong curvature forming two caps closing the helix cavity. 20 Based on previous results, 3 we anticipated that the elongation of these quinoline segments would cause a dramatic increase of the overall stability of the helix. Hence, we designed two new sequences which include either a quinoline pentamer (2) or a quinoline heptamer (3) at each end of the sequence.…”

Section: ■ Results and Discussionmentioning

confidence: 95%

Long-Range Effects on the Capture and Release of a Chiral Guest by a Helical Molecular Capsule

et al. 2012

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Helically folded molecular capsules based on oligoamide sequences of aromatic amino acids which are capable of binding tartaric acid in organic solvents with high affinity and diastereoselectivity have been synthesized, and their structures and binding properties investigated by (1)H NMR, X-ray crystallography, circular dichroism, and molecular modeling. We found that elongating the helices at their extremities by adding monomers remote from the tartaric binding site results in a strong increase of the overall helix stability, but it does not influence the host-guest complex stability. The effect of this elongation on the binding and release rates of the guest molecules follows an unexpected non-monotonous trend. Three independent observations (direct monitoring of exchange over time, 2D-EXSY NMR, and molecular modeling) concur and show that guest exchange rates tend to first increase upon increasing helix length and then decrease when helix length is increased further. This investigation thus reveals the complex effects of adding monomers in a helically folded sequence on a binding event that occurs at a remote site and sheds light on possible binding and release mechanisms.

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Section: ■ Results and Discussionmentioning

confidence: 95%

Long-Range Effects on the Capture and Release of a Chiral Guest by a Helical Molecular Capsule

et al. 2012

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“…Ever since the folding behaviors of m-phenylene ethynylene (mPE) oligomers were first reported by Moore and coworkers in 1997 [26], mPE and related arylene ethynylene foldamer systems have been extensively developed and investigated [27][28][29][30][31][32][33][34][35][36][37][38][39]. Compared with many other foldamer systems containing non-natural, aromatic units, such as aromatic oligoamides [15,16,[40][41][42][43], arylene polymer/oligomers [21,24,25,[44][45][46][47][48][49][50][51][52][53][54][55], poly(phenylacetylene)s [21,23,[56][57][58], iso-polydiacetylenes [59,60], poly(N-propargylamides) [61], poly(N-octylcarbazole ethylene) [62], polydiacetylene [63], etc., arylene ethynylene foldable systems (AEFS) exhibit a distinct feature that they mainly rely on weak, noncovalent interactions among non-adjacent backbone units to realize folding...…”

Section: Introduction and Scopementioning

confidence: 99%

Recent advances in arylene ethynylene folding systems: Toward functioning

Yan

et al. 2010

Coordination Chemistry Reviews

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“…The interactions responsible for structural stabilization are almost exclusively non-cooperative, although cooperative interactions are possible between nonadjacent units (see Chapter 1). Linear [119][120][121], cyclic [122][123][124], crescent-shaped [125,126], and helical [125][126][127][128][129] aryl amides have all been reported. However, bioactivity has only been introduced into the linear extended aryl amides.…”

Section: Aryl Amides and Aryl Ureasmentioning

confidence: 99%