Determination of orientational isomerism in rhodium(ii) metallopeptides by pyrene fluorescence

Sambasivan, Ramya; Ball, Zachary T.

doi:10.1039/c2ob26667a

Cited by 16 publications

(19 citation statements)

References 28 publications

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“…Pyrene excimer fluorescence identified Rh 2 L21 2 -isoB as having antiparallel helices. 993 Enantioselectivities from the catalyzed insertion of PhMe 2 SiH into methyl α -diazophenylacetate were improved by 5–18% for four Cbz-protected peptide sequences upon addition of triphenylphos-phite. 994 …”

Section: De Novo Designmentioning

confidence: 99%

Protein Design: Toward Functional Metalloenzymes

et al. 2014

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Section: De Novo Designmentioning

confidence: 99%

Protein Design: Toward Functional Metalloenzymes

et al. 2014

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“…Ball demonstrated a strategy to utilize natural polypeptide ligands for the development of chiral dirhodium catalysts (Scheme 14). 34,35 Based on this strategy, a relatively poor initial "hit" of 45% ee was improved using parallel automated peptide synthesis. In addition, the combined effects of peptide libraries and facile dirhodium complexation proved to be efficient in the development of selective catalytic transformations.…”

Section: Review Organic and Biomolecular Chemistrymentioning

confidence: 99%

Recent progress in the catalytic carbene insertion reactions into the silicon–hydrogen bond

2017

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The following review will explore the historical development of Si-H bond insertion reactions, giving an up-to-date account on the metal catalysts often employed, in addition to an assessment of their strengths and weaknesses. Diazo compounds have great synthetic potential as versatile reagents for the formation of metal carbenes, allowing the selective formation of C-C and C-heteroatom bonds and thus the introduction of functional groups into organic molecules. C-Si bond-forming methods, that introduce silicon motifs into organic molecules, rely on catalysts derived from metals such as rhodium, copper, iridium, silver, ruthenium, and iron to achieve the desired activities and selectivities.

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“…As part of a program aimed at mimicking the properties of metalloenzymes [6][7][8][9][10] for developing asymmetric transition metal catalysts, [11][12][13] and for rhodium(II) carboxylate complexes in particular, we have demonstrated that peptides with two carboxylate side chains (glutamate or aspartate) serve as chelating ligands 12 for rhodium(II), allowing asymmetric catalytic reactions of diazo compounds. [14][15][16][17] Polypeptides are readily optimizable ligands for stereoselective catalysis owing to the chirality and structural variation present in amino acids. [18][19][20] Our initial efforts 14 developed screening methods that identied bispeptide complexes of the type Rh 2 (peptide) 2 .…”

Section: Introductionmentioning

confidence: 99%