2005
DOI: 10.1021/ol051179r
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Specific Autocatalysis in Diastereoisomeric Replicators

Abstract: Two diastereoisomeric cycloadducts are capable of accelerating their own formation through the assembly of catalytic ternary complexes. The two cycloadducts do not have any measurable catalytic effect on the rate of formation of their diastereoisomer. [structure: see text]

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Cited by 36 publications
(30 citation statements)
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“…More interestingly, there is a fundamental incongruence between exo-5 b and endo-5 b; no low-energy structure of [exo-5 b·endo-5 b] contains more than two hydrogen bonds and, therefore, it seems unlikely that one diastereoisomeric template could support the transition state for the other. This result may indicate that antagonistic diastereospecific replication cycles, similar to those reported previously by our group [23] , are operating in this system.…”
Section: Resultssupporting
confidence: 89%
“…More interestingly, there is a fundamental incongruence between exo-5 b and endo-5 b; no low-energy structure of [exo-5 b·endo-5 b] contains more than two hydrogen bonds and, therefore, it seems unlikely that one diastereoisomeric template could support the transition state for the other. This result may indicate that antagonistic diastereospecific replication cycles, similar to those reported previously by our group [23] , are operating in this system.…”
Section: Resultssupporting
confidence: 89%
“…[109][110][111][112] Das System ist hochempfindlich gegenüber Strukturveränderungen, so kann beispielsweise eine Methylengruppe den Unterschied ausmachen zwischen einer wirksamen Autokatalyse und Systemen, die konkurrierende Präassoziationsreaktionen erfahren. [109][110][111][112] Das System ist hochempfindlich gegenüber Strukturveränderungen, so kann beispielsweise eine Methylengruppe den Unterschied ausmachen zwischen einer wirksamen Autokatalyse und Systemen, die konkurrierende Präassoziationsreaktionen erfahren.…”
Section: Kleine Moleküleunclassified
“…Other groups have examined self-replicating Diels-Alder reactions [10,11] including von Kiedrowski [9]. In addition to the advantages of being capable of self-replicating by homochiral autocatalysis and heterochiral cross-catalysis, they are much more efficient replicators than nucleic acids or peptides, giving rise to almost exponential replication.…”
Section: Chemical Systems Capable Of Self-replicationmentioning
confidence: 99%