2015
DOI: 10.1002/chem.201501415
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Adaptive Correction from Virtually Complex Dynamic Libraries: The Role of Noncovalent Interactions in Structural Selection and Folding

Abstract: The hierarchical self-assembling of complex molecular systems is dictated by the chemical and structural information stored in their components. This information can be expressed through an adaptive process that determines the structurally fittest assembly under given environmental conditions. We have set up complex disulfide-based dynamic covalent libraries of chemically and topologically diverse pseudopeptidic compounds. We show how the reaction evolves from very complex mixtures at short reaction times to t… Show more

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Cited by 22 publications
(17 citation statements)
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“…We tentatively assigned this peak to the bis‐macrocyclic compound Ia . At three hours the library started to simplify and smoothly evolved to the unique formation of the final macrobicycle I a after 24 h, thus taking longer than other libraries previously reported in our group to reach a thermodynamic equilibrium . These data suggest that the formation of the main species is fairly complex and, again, this fact supports the formation of I b in detriment of I a , which was transiently formed rather quickly.…”
Section: Resultssupporting
confidence: 60%
See 1 more Smart Citation
“…We tentatively assigned this peak to the bis‐macrocyclic compound Ia . At three hours the library started to simplify and smoothly evolved to the unique formation of the final macrobicycle I a after 24 h, thus taking longer than other libraries previously reported in our group to reach a thermodynamic equilibrium . These data suggest that the formation of the main species is fairly complex and, again, this fact supports the formation of I b in detriment of I a , which was transiently formed rather quickly.…”
Section: Resultssupporting
confidence: 60%
“…To this aim, we began to investigate libraries obtained by mixing pseudopeptides with a different number of thiol functional groups, in other words, different ‘valence’ in the DCC process. In these libraries we could eventually observe self‐recognition processes able to drive the library towards the exclusive formation of a single structure . Later on, this knowledge allowed us to rationally design a dynamic chemical network that reorganizes in the presence of an analyte (cysteine or cystine) liberating a fluorescent compound as readable output.…”
Section: Introductionmentioning
confidence: 99%
“…Finally, molecular recognition followed by covalent trapping of a zwitterion has been observed to shift the equilibria in dynamic covalent libraries. Solà and Alfonso reported how the recognition of zwitterionic cysteine and its reaction by the free sulfide functional group leads to simplification of potentially complex mixtures . The authors later used this specificity to design a modified library that gives a fluorescent response in the presence of cysteine (or its oxidized dimer, cystine) and allows to detect this amino acid in aqueous environment and even in human urine …”
Section: Miscellaneous Receptorsmentioning
confidence: 99%
“…sulfide functional group leads to simplification of potentially complex mixtures. [66] The authors later used this specificity to design a modified library that gives a fluorescent response in the presence of cysteine (or its oxidized dimer, cystine) and allows to detect this amino acid in aqueous environment and even in human urine. [67]…”
Section: Miscellaneous Receptorsmentioning
confidence: 99%
“…[17] We discovered that mixing equimolar amounts of BB 1, 2,a nd 3a (Figure 1) at pH close to neutrality in aqueous media resulted in the almost exclusive assembly of the heterotrimer 4a.T his selectivity is due to the self-recognition mediated by non-covalent interactions between the different functionalities of the constituents ( Figure 1B). [17] We anticipated that by replacing cysteine( 3a)w ith ad ifferent monothiol containing af luorophore with al esser tendency to form the corresponding heterotrimer (3b), acomplex mixture would occur. Addition of 3a to this library would lead to the most stable 4a,w ith the concomitant redistribution of the dynamic mixture,r eleasing the fluorophore as its disulfide homodimer.T his conversion could be read in the fluorescence spectra due to the formation of excimers [18] ( Figure 1B).…”
mentioning
confidence: 93%