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Conformational versatility among crystalline solids of L-phenylalanine derivatives.
Acta Crystallogr C Struct Chem
February 2025
Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
In this study, we present a new N-derivative of L-phenylalanine with 2-naphthaldehyde (PN), obtained by the Schiff base formation procedure and its subsequent reduction. This compound was crystallized as a zwitterion {2-[(naphthalen-2-ylmethyl)azaniumyl]-3-phenylpropanoate, CHNO}, as an anion in a sodium salt (catena-poly[[diaquasodium(I)-di-μ-aqua] 2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoate monohydrate], {[Na(HO)](CHNO)·HO}), as a cation in a chloride salt [(1-carboxy-2-phenylethyl)(naphthalen-2-ylmethyl)azanium chloride acetic acid monosolvate, CHNO·Cl·CHCOOH], and additionally acting as a ligand in the pentacoordinated zinc compound aquabis{2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoato-κO}zinc(II), [Zn(CHNO)(HO)] or [Zn(PN)(HO)], denoted (PN-Zn), with the amino acid derivative in its carboxylate form.
View Article and Find Full Text PDFEnantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas.
Chirality
February 2025
Department of Chemistry, Bogazici University, Istanbul, Turkey.
2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1-4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NHSCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used.
View Article and Find Full Text PDFAutomated Flow Synthesis of Artificial Heme Enzymes for Enantiodivergent Biocatalysis.
J Am Chem Soc
January 2025
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
The remarkable efficiency with which enzymes catalyze small-molecule reactions has driven their widespread application in organic chemistry. Here, we employ automated fast-flow solid-phase synthesis to access catalytically active full-length enzymes without restrictions on the number and structure of noncanonical amino acids incorporated. We demonstrate the total syntheses of iron-dependent myoglobin (BsMb) and sperm whale myoglobin (SwMb).
View Article and Find Full Text PDFA two-dimensional liquid chromatography approach for simultaneous separation and quantification of structural and chiral amino acids in oolong tea.
Food Chem
January 2025
Mane SEA PTE LTD, 3 Biopolis Drive, #07-17/18/19 Synapse, 138623, Singapore. Electronic address:
Oolong tea contains diverse isomers, such as amino acids. D-amino acids, compared with their L-enantiomers, exhibit distinct properties, influencing both the flavor and bioactivity of the tea. However, the analysis of these isomers remains challenging, especially the simultaneous determination of structural and chiral isomers.
View Article and Find Full Text PDFEffect of the support alkyl chain nature in the functional properties of the immobilized lipases.
Enzyme Microb Technol
January 2025
Departamento de Biocatálisis, ICP-CSIC, C/Marie Curie 2, Campus UAM-CSIC, Cantoblanco, Madrid 28049, Spain. Electronic address:
Supports coated with amino-hexyl and amino octyl have been prepared from glyoxyl agarose beads and compared in their performance with octyl-agarose to immobilize lipases A and B from Candida antarctica (CALA and CALB). Immobilization courses were similar using all supports, but enzyme release was more difficult using the amino-alkyl supports suggesting a mixed interfacial activation/ionic exchange immobilization. The enzyme activity and specificity (using p-nitrophenyl propionate, triacetin and both isomers of methyl mandelate) greatly depended on the support.
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