Oligopeptides as catalysts for asymmetric epoxidation

Kelly, David R.; Roberts, Stanley M.

doi:10.1002/bip.20373

Cited by 86 publications

(25 citation statements)

References 131 publications

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“…One would rather say "complementarities" in plural as the complexes complementary in the Delbrück-Pauling sense could have been formed, as well between abiotically synthesized peptides (e.g., Lahav et al, 1978 ) and between the peptides and RNA. Catalytic properties of peptides (Kelly and Roberts, 2006 ) and RNA (Doudna and Cech, 2002 ) only add to the opening of the vast spectrum of molecular competitions, making the emergence of complementary replication of RNA more real.…”

Section: Complementarity Enters the Scenementioning

confidence: 99%

Disorder to Order, Nonlife to Life: In the Beginning There Was a Mistake

Mauro

Dunker

Trifonov

2012

Cellular Origin, Life in Extreme Habitats and Astrobiology

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is professor of Molecular Biology at the University "Sapienza" of Rome. His research activity has been consistently focused on the study of the structure and of the function of genetic materials, in both prokaryotes and eukaryotes.Contributions were made in the fi elds of DNA topology and of topologyrelated functions, in the biophysics and biochemistry of gene expression. Special interest was devoted to the kinetic and topological aspects of gene regulation. Part of his research has dealt with the study of plausible prebiotic routes to the evolution of informational macromolecules. This latter approach has lead to the discovery of reactions affording the prebiotic synthesis of a complete set of nucleic acid precursors. The study of novel chemical mechanisms in an originof-life scenario is at present one of the main interests of his research group, recently leading to the discovery of the abiotic generation of long RNA molecules in water. E-mail: ernesto.dimauro@uniroma1.it 416 ERNESTO DI MAURO ET AL. Prof. A. Keith Dunker is the Director of the Center for ComputationalBiology and Bioinformatics at the Indiana University School of Medicine. His life-long interests have been in protein structure-function relationships using virus or phage structure, assembly and cell penetration as model systems for study. In the mid-1990s, from clues provided by mechanisms of host cell penetration by filamentous phage, Dr. Dunker and his collaborators began to use computational approaches to study proteins that utilize lack of structure rather than structure to carry out biological function. This work, which is continuing up to the present, suggests that the sequence-to-structure-to-function paradigm applies mainly to enzymes and membrane transport proteins while a new paradigm, sequenceto-unstructured, dynamic protein ensemble-to-function applies to proteins and regions of proteins that carry out control, regulation, and signaling.

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Section: Complementarity Enters the Scenementioning

confidence: 99%

Disorder to Order, Nonlife to Life: In the Beginning There Was a Mistake

Mauro

Dunker

Trifonov

2012

Cellular Origin, Life in Extreme Habitats and Astrobiology

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“…[3] One of the early demonstrations of chiral polymers in catalysis was the use of polypeptides as catalysts in the enantioselective nucleophilic epoxidation of chalcone with hydrogen peroxide, in what has become known as the Julia-Colonna epoxidation. [5][6][7][8] Using polyalanine as the catalyst, the epoxide product could be obtained in up to 96 % enantiomeric excess (ee), depending on the length of the polypeptide (Scheme 1). This was the first indication of a macromolecular amplification of chirality, although a helical structure has not been proven for these peptides.…”

Section: Static Helical Polymersmentioning

confidence: 99%

Asymmetric Catalysis with Helical Polymers

Megens

Roelfes

2011

Chemistry A European J

157

106

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“…[9] Over the years, this reaction, which is promoted by homo-oligopeptides, has been intensively investigated by different groups and significant improvements have been reached in terms of practicality [10] as well as in the understanding of the mechanism of asymmetric induction. [11] Recently, notable results have been achieved in the asymmetric epoxidation of α,β-unsaturated aldehydes, a challenging transformation, which was promoted by simple O-protected diaryl-2-pyrrolidinemethanols in the presence of aqueous H 2 O 2 as the oxidant.…”

Section: Introductionmentioning

confidence: 99%