Development of Selective Peptide Catalysts with Secondary Structural Frameworks

The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst with furfuryl alcohol, thus rendering polyfurfuryl alcohol-supported catalysts for applications in heterogeneous enamine catalysis. The utilization of the polymer-supported catalysts in both batch and continuous-flow organocatalytic procedures proved moderate catalytic efficacy and enantioselectivity, but excellent diastereoselectivity in the asymmetric Michael addition of n-butanal to β-nitrostyrene that was used as a model reaction. This work supports the potential of multicomponent reactions towards the assembly of catalysts and their simultaneous functionalization for immobilization.

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Novel stereoselective incorporation and hydrolysis of long-chain amino-acid substrates by vesicular membrane systems which include tri- or tetra-peptide catalysts

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19950002957 ◽

1995 ◽

pp. 2957 ◽

Cited By ~ 2

Author(s):

Katsutoshi Ohkubo ◽

Kenji Urabe ◽

Junji Yamamoto ◽

Takashi Sagawa ◽

Satoshi Usui

Keyword(s):

Amino Acid ◽

Membrane Systems ◽

Peptide Catalysts ◽

Vesicular Membrane ◽

Hydrolysis Of ◽

Long Chain

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Design of Peptide Catalysts by Combining Secondary Structural Units for Selective Reactions

Journal of Synthetic Organic Chemistry Japan ◽

10.5059/yukigoseikyokaishi.77.1222 ◽

2019 ◽

Vol 77 (12) ◽

pp. 1222-1233

Author(s):

Kengo Akagawa ◽

Kazuaki Kudo

Keyword(s):

Structural Units ◽

Peptide Catalysts

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Efficient multi-point interaction between peptide catalysts and amino acid esters in a bilayer vesicular membrane for highly stereoselective hydrolysis reactions

Journal of the Chemical Society Chemical Communications ◽

10.1039/c39950002301 ◽

1995 ◽

pp. 2301 ◽

Cited By ~ 1

Author(s):

Katsutoshi Ohkubo ◽

Kenji Urabe ◽

Junji Yamamoto ◽

Hitoshi Ishida ◽

Satoshi Usui ◽

...

Keyword(s):

Amino Acid ◽

Point Interaction ◽

Amino Acid Esters ◽

Peptide Catalysts ◽

Vesicular Membrane ◽

Stereoselective Hydrolysis ◽

Acid Esters ◽

Hydrolysis Reactions

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Multicomponent Approach to Silica-Grafted Peptide Catalysts: A 3 D Continuous-Flow Organocatalytic System with On-line Monitoring of Conversion and Stereoselectivity

ChemCatChem ◽

10.1002/cctc.201402501 ◽

2014 ◽

Vol 6 (11) ◽

pp. 3208-3214 ◽

Cited By ~ 16

Author(s):

Gabriel S. Scatena ◽

Alexander F. de la Torre ◽

Quezia B. Cass ◽

Daniel G. Rivera ◽

Márcio W. Paixão

Keyword(s):

Continuous Flow ◽

Peptide Catalysts ◽

On Line

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Polypeptide-catalyzed Biosilicification of Dentin Surfaces

Journal of Dental Research ◽

10.1177/0022034509333838 ◽

2009 ◽

Vol 88 (4) ◽

pp. 377-381 ◽

Cited By ~ 7

Author(s):

A.J. Goldberg ◽

M.C. Advincula ◽

T. Komabayashi ◽

P.A. Patel ◽

P.T. Mather ◽

...

Keyword(s):

Photoelectron Spectroscopy ◽

Treatment Strategies ◽

Marine Species ◽

X Ray ◽

Mineral Particles ◽

Peptide Catalysts ◽

Wide Range ◽

Negative Controls ◽

Peptide Catalyst

In situ formation of mineral particles by biocatalysis would be advantageous for occluding dentin tubules to reduce permeability or for sealing of material-tooth interfaces. One approach would require that the peptide-catalyst remain functional on the dentin surface. Based on recent observations of retained activity on other surfaces, we hypothesized that poly(L-lysine) (PLL), an analog of the protein catalyst responsible for silica formation in primitive marine species, would remain functional on dentin. PLL was applied to dentin discs along with a pre-hydrolyzed silica precursor, tetramethyl orthosilicate (TMOS). Discs were analyzed microscopically (scanning electron microscopy, SEM) and chemically (x-ray photoelectron spectroscopy, XPS). The treated discs, but not the negative controls, exhibited partial distinct coating whose XPS survey was consistent with that of silica, demonstrating that the polypeptide was required and retained its mediating activity. Peptide-catalysts that mediate mineral formation can retain functionality on dentin, suggesting a wide range of preventive and treatment strategies.

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