Seven diastereomer pairs of tetrapeptide analogues (TP) of endomorphin-1 and -2 were synthesized. A stereoselective capillary electrophoretic method was developed for controlling stereoisomeric ratio or purity. The isoelectric points of the tetrapeptides were between 8.3 and 8.9 as predicted and measured. A few of the analytes could be resolved without selectors due to the difference in their mobility. Neutral and anionic cyclodextrins (CDs) were applied in order to improve resolution. Stability constants as well as the mobilities of complexes were determined. Contributions of differences in the mobilities of free analytes and in the mobilities and stabilities of their complexes formed by CDs were equally important in the efficient resolution and migration order of diastereomers. As a result of the optimization of the pH of buffers and the concentration of the CD derivatives each diastereomer pair was resolved at baseline at least or better.
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http://dx.doi.org/10.1016/j.jpba.2012.05.013 | DOI Listing |
In this review we have compiled multicomponent reactions (MCRs) that produce cyclic structures. We have covered articles reported since 2019 to showcase the recent advances in this area. In contrast to other available reviews on this topic, we focus specifically on MCRs with strong prospects in medicinal chemistry.
View Article and Find Full Text PDFJ Biotechnol
January 2025
Key Laboratory of Industrial Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, Jiangsu 214122, China; The Research Center of Chiral Drugs, Shanghai Frontiers Science Center for TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China. Electronic address:
Chiral azacyclic amine derivatives occupy a vital role of nitrogen-containing compounds, due to serve as foundational motifs in numerous pharmaceuticals and bioactive substances. Novel complementary enantioselective reductive aminases IRED9 and IRED11 were unveiled through comprehensive gene mining from Streptomyces viridochromogenes and Micromonospora echinaurantiaca, respectively, which both demonstrated enantiomeric excess (ee) values and conversion ratios of up to 99 % towards N-Boc-3-pyridinone (NBPO) and cyclopropylamine. IRED9 exhibited the highest activity at pH 8.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Ni-catalyzed asymmetric reductive cross-coupling reactions provide rapid and modular access to enantioenriched building blocks from simple electrophile precursors. Reductive coupling reactions that can diverge through a common organometallic intermediate to two distinct families of enantioenriched products are particularly versatile but underdeveloped. Here, we describe the development of a bis(oxazoline) ligand that enables the desymmetrization of -anhydrides.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Jain University - Ramanagara Campus, Centre for Nano and Material Sciences, Jakkasandra Post Kanakapura Taluk, Ramanagara-562112, Bangalore, 562112, Bangalore, INDIA.
The development of a metallic copper-based catalyst system remains a significant challenge. Herein, we report the synthesis of highly stable, active, and reusable Cu0 catalyst for the carboboration of alkynes using carbon electrophiles and bis(pinacolato)diboron (B2pin2) as chemical feedstocks to afford di- and trisubstituted vinylboronate esters in a regio- and stereoselective manner with appreciable turnover number (TON) of up to 2535 under mild reaction conditions. This three-component coupling reaction works well with a variety of substituted electrophiles and alkynes with broad functional group tolerance.
View Article and Find Full Text PDFChirality
January 2025
Department of Pesticide Science, College of Plant Protection, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing Agricultural University, Nanjing, China.
Chiral pesticides often undergo enantioselective degradation during food fermentation. In this study, the enantioselective fates of seven chiral pesticides during processing of wine and rice wine were investigated. The results revealed that R-metalaxyl, R-mefentrifluconazole and S-hexaconazole were preferentially degraded during wine processing with EF values of 0.
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