Diastereoselective Amplification of an Induced-Fit Receptor from a Dynamic Combinatorial Library

Abstract

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Dynamic Combinatorial Chemistry: The Unexpected Choice of Receptors by Guest Molecules

“…This unexpected result, which is unlikely to have been discovered by traditional strategies, was explained by the induced-fit character of the host; meso-11 encapsulates the NMe þ 4 ion by folding completely around it (Figure 4). [11] Although "selection of the fittest" from a DCL does not necessarily always provide the "fittest", the importance of dynamic combinatorial chemistry is clearer than ever before. DCLs are theoretically well understood now and it is clear that they behave as complex systems.…”

“…The host binds the guest through an induced-fit mechanism. Reprinted with permission from Reference [11] …”

“…A common feature of these examples is that the hosts have unexpected structures, and it is very unlikely that these receptors would have been discovered by more traditional design and synthesis strategies. [11,7] For example, the DCL depicted in Figure 2 is Table 1: Free-energy "economics" in the relative concentrations (c rel ) of library members of type B (Figure 1) as a function Figure 2. Unexpected amplification of a catenane receptor from a DCL of cyclic peptides by the addition of the neurotransmitter acetylcholine.…”

Dynamische kombinatorische Chemie: die überraschende Rezeptorwahl durch Gastmoleküle

“…Die [11,7] Beispielsweise entsteht die in Abbildung 2 dargestellte DCL durch reversible Bildung eines Hydrazons aus der Hydrazidfunktion und einer als Acetal geschützten Aldehydeinheit des Prolin-Phenylalanin-Pseudopeptids pPFm (1). Die Bibliothek besteht hauptsächlich aus den cyclischen Oligomeren 2-5 (insbesondere 2-4).…”

“…Unvermutete Anreicherung eines großen cyclischen Wirtmoleküls in einer DCL nach der Zugabe von NMe 4 + . [11] Abbildung 4. Kalottenmodelle des Komplexes von meso-11 und NMe 4 + zeigen die ausgebreitete (a) und die gefaltete Konformation (b).…”