Molecular amplification in a dynamic system by ammonium cations

Furlán, Ricardo L. E.; Ng, Yiu‐Fai; Cousins, Graham R. L.; Redman, James E.; Sanders, Jeremy K. M.

doi:10.1016/s0040-4020(01)01102-4

Cited by 54 publications

(33 citation statements)

References 42 publications

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“…Tributyl-or triethylammonium salts produced weak nonspecific amplification of higher oligomers. 158 Binding constants between the cyclic trimer and the two templates were estimated to be relatively small: 150 and 230 M -1 for 27 and 28, respectively. 158 In comparison, Kubik's cyclic peptides bind 27 and 28 with binding constants of 4.22 × 10 4 M -1 and 1.10 × 10 4 M -1 in pure chloroform.…”

Section: Scheme 37 Formation Of a DCL Of Cyclic Oligoimines Followedmentioning

confidence: 98%

Dynamic Combinatorial Chemistry

et al. 2006

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Section: Scheme 37 Formation Of a DCL Of Cyclic Oligoimines Followedmentioning

confidence: 98%

Dynamic Combinatorial Chemistry

et al. 2006

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“…Binding constants for the complexes between the selected trimer and the different templates correlate well with the effects these templates have on the product distribution [63] . Unfortunately, the binding constants that are driving amplifi cation cannot be measured for this system since the necessary acidity to reproduce exact conditions for binding will catalyze the degradation of receptor 17 to produce cyclic dimer in an extent that will depend on the amount of template present.…”

Section: Ensuring Meaningful Amplifi Cationsmentioning

confidence: 70%

“…An equivalent experiment for DCLs prepared from a single building block is to isolate one library member and demonstrate that upon exposing it to the exchange conditions, it regenerates a library identical to that from which it was isolated [45,62,63] .…”

Section: Assessing Equilibriummentioning

confidence: 99%

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Development of Synthetic Receptors using Dynamic Combinatorial Chemistry

Escalante

Furlán

2010

Dynamic Combinatorial Chemistry

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In order to bind a given guest, a receptor must be complementary -it must have recognition groups which are of the appropriate electronic character to complement the binding sites of the guest. Those recognition groups must be positioned on the receptor in a way that they can interact with recognition groups from the guest when both receptor and guest are in the binding conformation. Upon binding, the receptor and guest reorganize their interactions with solvent molecules (disrupting some and probably creating new ones), and change their conformation to achieve a suitable binding conformation. In the process, noncovalent interactions within each molecule may be broken or formed.The requirement to balance all the variables involved in this recognition process makes the design of successful synthetic receptors a signifi cant challenge.A frequently explored shortcut that facilitates receptor design is to incorporate rigidity in order to avoid as much as possible changes in conformation that are diffi cult to predict. In addition, a rigid preorganized receptor will decrease the cost of unfavorable reorganization energy. However, high -affi nity perfectly rigid receptors are not easy to achieve in practice since minor errors in design that demand readjustment from the receptor can be energetically very expensive [1] . Indeed, nature does not use rigidity to improve affi nity, but it still produces receptors with affi nities that are on average much better than the best synthetic receptors prepared to date. A recent survey of the binding effi ciency of synthetic and biological hosts by Houk et al. indicates that synthetic systems are typically several orders of magnitude less effi cient in binding small molecules than their biological counterparts [2] .Guest binding by natural receptors such as proteins is reinforced by intrareceptor interactions, which require conformational rearrangements of parts of the receptor that are very similar to the conformational rearrangement necessary to interact with the guest. Consequently the interactions that contribute to guest binding extend beyond the immediate binding site well into the protein structure [3] . Synthetic receptors that operate by the same principle will need to be able to Dynamic Combinatorial Chemistry. Edited by Joost N. H. Reek and Sijbren Otto

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“…Exposure of these libraries to templates has resulted in dramatic shifts in the distribution of the library in a number of cases (6,(24)(25)(26)(27). In one instance (26), cyclization of building block 13 derived from L-proline-Lphenylalanine in chloroform solution initially produced a mixture of at least 10 interconverting macrocycles.…”

Section: Templating Dynamic Combinatorial Librariesmentioning

confidence: 99%