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Cyclodextrin-based class I aldolase enzyme mimics to catalyze crossed aldol condensations

A variety of mono- and unsymmetrical bifunctional beta-cyclodextrins have been developed as efficient mimics of class I aldolases, some of which show a large rate acceleration and substrate selectivity.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Process for the stereoselective preparation of l-alanyl-l-proline

L-alanyl-L-proline is stereoselectively prepared catalytically hydrogenating an N-(2-iminopropionyl)-L-proline in the presence of a metal hydrogenolysis catalyst and at a pH of less than about 4. Also disclosed are improved processes for production of N-pyruvyl-L-proline in which L-proline and a 2,2-disubstituted propionyl halide are allowed to react at a pH of at least 9 to produce an L-proline intermediate which is hydrolyzed at a pH range of from about 6.5 to about 8.5 to yield N-pyruvyl-L-proline.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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CHAPTER 9: Potential of CE-MS for Chiral Metabolic Profiling

Despite the not-so-straightforward coupling of chiral capillary electrophoresis (CE) to mass spectrometry (MS), this approach has been shown to offer numerous possibilities in the past few years. The applicability of chiral CE-MS to the emerging metabolomics field has not been exploited in full detail yet. In this context, the application of CE-MS for chiral metabolomics has only been focused on targeted studies, mainly for the investigation of the enantioselective metabolism of drugs and/or other molecules. This indicates that non-targeted studies have not yet been implemented using this technique. This work discusses those targeted contributions using CE-MS for chiral metabolic profiling studies. In addition, potential strategies to carry out studies of metabolic profiles are included. Future trends should involve improvement in robustness and sensitivity, and development of new chiral selectors compatible with MS detection. These improvements are expected to open up new possibilities for a more solid implementation of CE-MS in chiral metabolomics.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Inhibitors of tripeptidyl peptidase II. 2. Generation of the first novel lead inhibitor of cholecystokinin-8-inactivating peptidase: A strategy for the design of peptidase inhibitors

The cholecystokinin-8 (CCK-8)-inactivating peptidase is a serine peptidase which has been shown to be a membrane-bound isoform of tripeptidyl peptidase II (EC 3.4.14.10). It cleaves the neurotransmitter CCK-8 sulfate at the Met-Gly bond to give Asp-Tyr(SO3H)-Met-OH + Gly-Trp-Met-Asp-Phe-NH2. In seeking a reversible inhibitor of this peptidase, the enzymatic binding subsites were characterized using a fluorimetric assay based on the hydrolysis of the artificial substrate Ala-Ala-Phe-amidomethylcoumarin. A series of di- and tripeptides having various alkyl or aryl side chains was studied to determine the accessible volume for binding and to probe the potential for hydrophobic interactions. From this initial study the tripeptides Ile-Pro-Ile-OH (K(i) = 1 muM) and Ala-Pro-Ala-OH (K(i) = 3 muM) and dipeptide amide Val-Nvl-NHBu (K(i) = 3 muM) emerged as leads. Comparison of these structures led to the synthesis of Val-Pro-NHBu (K(i) = 0.57 muM) which served for later optimization in the design of butabindide, a potent reversible competitive and selective inhibitor of the CCK-8-inactivating peptidase. The strategy for this work is explicitly described since it illustrates a possible general approach for peptidase inhibitor design.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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5-aminomethylquinoxaline-2,3-diones. Part 1: A novel class of ampa receptor antagonists.

A series of 5-aminomethylquinoxaline-2,3-diones have been identified as potent and selective AMPA antagonists. Some of these compounds are also active at the glycine-binding site of the NMDA receptors. A number of these novel, water-soluble quinoxaline-2,3-dione derivatives display protective effects in the electroshock-induced convulsion model in mice.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Archives for Chemistry Experiments of H-D-Pro-OH

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Chromatographic Resolution of alpha-Amino Acids by (R)-(3,3′-Halogen Substituted-1,1′-binaphthyl)-20-crown-6 Stationary Phase in HPLC

Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3′-halogen substituted-1,1′-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one alpha-amino acids have different degrees of separation on R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1′-binaphthyl)-20-crown-6 derivatives. Both the separation factors (alpha) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6 chiral stationary phase.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI