Artificial Metalloenzymes for Enantioselective Catalysis Based on the Biotin–Avidin Technology

Mao, Jincheng; Ward, Thomas R.

doi:10.1007/978-3-540-87757-8_5

Cited by 10 publications

(4 citation statements)

References 72 publications

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“…By far and away, the most studied approach to generate ArMs for organic catalysis via noncovalent interactions (or perhaps via any means) involves binding biotin-substituted cofactors to avidin (Avi) or streptavidin (Sav) scaffolds, collectively (strept)avidin (Scheme B). − This approach is facilitated by the tight binding of biotin to (strept)avidin ( K d = 10 –12 –10 –15 M), which ensures rapid and essentially quantitative ArM formation, and the ease with which biotin can be attached to a range of metal complexes. In 1978, Whitesides demonstrated the first example of enantioselective ArM catalysis using biotinylated Rh–bisphosphine complex 24 (Scheme ) bound to Avi for hydrogenation of 2-acetamidoacrylate (∼40% ee, S enantiomer) .…”

Section: Artificial Metalloenzymesmentioning

confidence: 99%

Artificial Metalloenzymes and Metallopeptide Catalysts for Organic Synthesis

2013

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Transition metal catalysts and enzymes possess unique and often complementary properties that have made them important tools for chemical synthesis. The potential practical benefits of catalysts that combine these properties and a desire to understand how the structure and reactivity of metal and peptide components affect each other have driven researchers to create hybrid metal−peptide catalysts since the 1970s. The hybrid catalysts developed to date possess unique compositions of matter at the inorganic/biological interface that often pose significant challenges from design, synthesis, and characterization perspectives. Despite these obstacles, researchers have developed systems in which secondary coordination sphere effects impart selectivity to metal catalysts, accelerate chemical reactions, and are systematically optimized via directed evolution. This perspective outlines fundamental principles, key developments, and future prospects for the design, preparation, and application of peptide-and protein-based hybrid catalysts for organic transformations.

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Section: Artificial Metalloenzymesmentioning

confidence: 99%

Artificial Metalloenzymes and Metallopeptide Catalysts for Organic Synthesis

2013

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“…Structural variants of protein scaffold can nowadays easily be generated using advanced mutagenesis strategies. Whereas most of the systems to date have only been subjected to limited mutagenesis to tune their performance, the studies of Ward and Reetz on the avidin–biotin system highlight the potential of evolving systems by the combinatorial screening of large numbers of mutant proteins 110…”

Section: Artificial Metalloenzymesmentioning

confidence: 99%

Anion‐Driven Reversible Switching of Metal‐Centered Stereoisomers in Metallopeptides

Ousaka¹,

Takeyama²,

Yashima³

2013

Chemistry A European J

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Anion-triggered chiral switch: Reversible switching between fac and mer isomers in tris(2,2'-bipyridine)iron(II) complexes, the ligands of which are substituted at the 5-position with various peptides of different lengths and sequences, has been achieved (see figure). The remote stereocontrol at the Fe II center by a domino-type chiral information transfer along an achiral peptide main-chain was observed even over 3 nm (50 bond lengths). Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/ threonines and cysteines.ChemBioChem

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“…J. [110] Directed evolution is a very powerful tool for the optimisation of the properties of proteins, which is increasingly applied to improve enzyme performance and protein properties. [111] This approach uses repeating cycles of random mutagenesis followed by screening for the best hits in a Darwinian fashion.…”

Section: Optimisation Techniques For Artificial Metalloenzymesmentioning

confidence: 99%

Bioinspired Catalyst Design and Artificial Metalloenzymes

Deuss

Heeten

Laan

et al. 2011

Chemistry A European J

181

124

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Many bioinspired transition-metal catalysts have been developed over the recent years. In this review the progress in the design and application of ligand systems based on peptides and DNA and the development of artificial metalloenzymes are reviewed with a particular emphasis on the combination of phosphane ligands with powerful molecular recognition and shape selectivity of biomolecules. The various approaches for the assembly of these catalytic systems will be highlighted, and the possibilities that the use of the building blocks of Nature provide for catalyst optimisation strategies are discussed.

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Artificial Metalloenzymes for Enantioselective Catalysis Based on the Biotin–Avidin Technology

Cited by 10 publications

References 72 publications

Artificial Metalloenzymes and Metallopeptide Catalysts for Organic Synthesis

Artificial Metalloenzymes and Metallopeptide Catalysts for Organic Synthesis

Anion‐Driven Reversible Switching of Metal‐Centered Stereoisomers in Metallopeptides

Bioinspired Catalyst Design and Artificial Metalloenzymes

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