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Although d-amino acids are less prevalent in nature, they have been detected in mammals (including humans) and it is widely accepted that they might play important physiological roles. While an analytical method for chiral amino acid profiling is strongly required, it has not been well-established because of the difficulties associated with analysis. A high-sensitivity and high-throughput liquid chromatography-tandem mass spectrometry (LC-MS/MS) analytical method was recently reported by our group for chiral amino acids; however, it lacked sufficient repeatability for several d-amino acids. Thus, the aim of this research was to reduce the experimental variation of chiral amino acid analysis. By installing an automatic switching valve system in LC-MS/MS, it was possible to reduce the relative standard deviations of d-amino acid ratios (d/(d+l)) in rat urine obtained from three technical replicates. The results indicated that the automatic switching valve system was effective in minimizing the variation of d-amino acid ratios, and could be applied for profiling d-amino acids because of its high repeatability.
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http://dx.doi.org/10.1016/j.jbiosc.2019.06.005 | DOI Listing |
Chem Commun (Camb)
September 2025
International Joint Research Centre for Molecular Science, College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen, 518060, P. R. China.
Deuterated compounds possess significant research value. As interest in chiral deuterated compounds intensifies, various deuteration methods are garnering increased attention. This article primarily reviews the asymmetric deuterium synthesis methods reported in recent years, focusing on the following strategies: one-step reductive deuteration, the series reaction of H/D exchange and asymmetric allylation, the [3+2] asymmetric cycloaddition of 1,3-dipoles and alkenes, asymmetric deuteration photocatalysis, asymmetric deuteration using organic catalysis, and asymmetric deuteration of chiral amino acids and their derivatives through biocatalysis.
View Article and Find Full Text PDFOrg Lett
September 2025
Frontiers Science Center for Transformative Molecules, State Key Laboratory of Polyolefins and Catalysis, State Key Laboratory of Synergistic Chem-Bio Synthesis, Zhang Jiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, China.
C-labeled α-amino acids are important molecules in biological studies and drug development. Cost-effective synthesis of α-amino acids with a high level of C incorporation under mild conditions remains limited. Herein, we report the development of a benzylic C(sp)-H carboxylation method to prepare highly C-labeled α-amino acids, i.
View Article and Find Full Text PDFOrg Lett
September 2025
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Ahmedabad, Gujarat 382355, India.
Herein, we report an easily tunable and regioselective Pd-catalyzed allene-alkyne coupling protocol for the stereodivergent synthesis of - and -1,3-enynes using purine allenamine by a simple switch of ligands P(-tolyl)Ph and Boc-Phe-OH. For the first time, we have explored mono--protected amino acids (MPAAs) as ligands in allene-alkyne coupling to furnish -1,3-enynes selectively. This protocol streamlined the access to chiral 1,3-enynes and addressed the long-standing stereoselectivity challenges associated with 1,3-enynes from allene-alkyne coupling.
View Article and Find Full Text PDFOrg Lett
September 2025
State Key Laboratory of Chemistry for NBC Hazards Protection, Beijing 102205, China.
Optically active α-aminophosphonic acids are unique analogues of α-amino acids, and numerous synthetic methods have been developed. Herein, we present a highly diastereoselective α-azidation approach to the CAMDOL-derived phosphonates, enabling ready access to 27 diverse α-azidophosphonates with defined chirality in up to 85% yield and more than 99:1 dr. Late-stage transformations through the Staudinger reaction or click reaction efficiently delivered the related pharmacological α-aminophosphonic acids or the unique α-triazolylphosphonate derivative, respectively.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
Center for Chemical Glycobiology, Shanghai Key Laboratory for Antibody-Drug Conjugates with Innovative Target, State Key Laboratory of Synergistic Chem-Bio Synthesis, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China.
The ability to selectively cleave C-heteroatom bonds is critically important in chemical science, from peptide and protein synthesis to biomolecule manipulation. For example, C-heteroatom bond cleavage is widely used in fluorenylmethyloxycarbonyl/-butyl (Fmoc/Bu)-based solid-phase peptide synthesis (SPPS). Despite its usefulness, it has inextricable limitations, such as issues with hydrophobicity and side reactions, owing to the need for the use of a strong trifluoroacetic acid (TFA, a pervasive forever chemical) as the cleavage reagent.
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