Cyclic decapeptide gramicidin S derivatives containing phosphines: novel ligands for asymmetric catalysis

Guisado‐Barrios, Gregorio; Muñoz, Bianca K.; Kamer, Paul C. J.; Lastdrager, Bas; Marel, Gijs van der; Overhand, Mark; Vega-Vázquez, Marino; Martín-Pastor, Manuel

doi:10.1039/c2dt31782f

Cited by 21 publications

(8 citation statements)

References 40 publications

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“…[33] b) Structures applied in palladium-catalysed asymmetric allylic substitution and rhodium-catalysed asymmetric hydrogenation. [34] www.chemeurj.org leaching was significantly reduced by positioning the phosphane ligands at different sites in the dendrimer interior, which allowed several recycling cycles in hydroformylation. [36] In the above sections several methods for mimicking enzymes using short synthetic peptides have been described.…”

Section: Other Oligopeptide Design Strategiesmentioning

confidence: 98%

“…(Scheme 5 b). [34] Rhodium complexes of these cyclic peptides were characterised and used as hydrogenation catalysts, resulting in moderate enantioselectivities (up to 52 % R) using the meta-substituted cyclic peptide. Interestingly the opposite enantiomers were obtained in low ee when the para-substituted cyclic peptide was used.…”

Section: Oligopeptide-modified Phosphane Ligandsmentioning

confidence: 99%

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Bioinspired Catalyst Design and Artificial Metalloenzymes

Deuss

Heeten

Laan

et al. 2011

Chemistry A European J

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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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Section: Other Oligopeptide Design Strategiesmentioning

confidence: 98%

Section: Oligopeptide-modified Phosphane Ligandsmentioning

confidence: 99%

Bioinspired Catalyst Design and Artificial Metalloenzymes

Deuss

Heeten

Laan

et al. 2011

Chemistry A European J

Self Cite

181

124

View full text Add to dashboard Cite

show abstract

“…On the other hand, oligo‐ and polypeptides with natural aspartic acid side chains and nonnatural amino acids with phosphine or pyridine functions were complexed with metal ions to act as catalysts in enantioselective organic transformations 5. The peptide scaffolds included metal‐chelating helical5a or β‐turn structures,5b oriented β‐turns,5c self‐assembled β‐sheet motifs,5d and natural polypeptide folds 5e,f. However, peptide scaffolds with little sequence constriction and flexibility in the amino acid composition remain elusive.…”

Section: Alanine Scanning Data For L5[a]mentioning

confidence: 99%

Conformationally Constrained Cyclic Peptides: Powerful Scaffolds for Asymmetric Catalysis

et al. 2014

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Cyclic peptides containing a disulfide bridge were identified as a simple and versatile coordination sphere for asymmetric catalysis. Upon complexation with Cu2+ ions they catalyze Diels–Alder and Friedel–Crafts reactions with high enantioselectivities of up to 99 % ee and 86 % ee, respectively. Moreover, the peptides ligands were systematically optimized with the assistance of “Alanine Scanning”. This biomolecular design could greatly expand the choice of peptide scaffolds for artificial metallopeptide catalysts.

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“…In between these two extremes lie metallopeptides. Peptides are able to form a number of conformationally constrained structures, α-helices [7,8], β-loops and sheets [9][10][11][12][13], coiled coils [14], and macrocycles [15][16][17][18], which have been shown to be to be beneficial in asymmetric catalysis [19][20][21][22]. As well as finding use in catalysis, metallopeptides have been studied extensively in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Macrocylases as synthetic tools for ligand synthesis: enzymatic synthesis of cyclic peptides containing metal-binding amino acids

et al. 2021

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Improving the sustainability of synthesis is a major goal in green chemistry, which has been greatly aided by the development of asymmetric transition metal catalysis. Recent advances in asymmetric catalysis show that the ability to control the coordination sphere of substrates can lead to improvements in enantioselectivity and activity, in a manner resembling the operation of enzymes. Peptides can be used to mimic enzyme structures and their secondary interactions and they are easily accessible through solid-phase peptide synthesis. Despite this, cyclic peptides remain underexplored as chiral ligands for catalysis due to synthetic complications upon macrocyclization. Here, we show that the solid-phase synthesis of peptides containing metal-binding amino acids, bipyridylalanine ( 1 ), phenyl pyridylalanine ( 2 ) and N,N- dimethylhistidine ( 3 ) can be combined with peptide macrocylization using peptide cyclase 1 (PCY1) to yield cyclic peptides under mild conditions. High conversions of the linear peptides were observed (approx. 90%) and the Cu-bound cyclo(FSAS( 1 )SSKP) was shown to be a competent catalyst in the Friedel-Crafts/conjugate addition of indole. This study shows that PCY1 can tolerate peptides containing amino acids with classic inorganic and organometallic ligands as side chains, opening the door to the streamlined and efficient development of cyclic peptides as metal ligands.

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Cyclic decapeptide gramicidin S derivatives containing phosphines: novel ligands for asymmetric catalysis

Cited by 21 publications

References 40 publications

Bioinspired Catalyst Design and Artificial Metalloenzymes

Bioinspired Catalyst Design and Artificial Metalloenzymes

Conformationally Constrained Cyclic Peptides: Powerful Scaffolds for Asymmetric Catalysis

Macrocylases as synthetic tools for ligand synthesis: enzymatic synthesis of cyclic peptides containing metal-binding amino acids

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