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• W2897518504 endingPage "13887" @default.
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• W2897518504 abstract "Enantiomers of a series of tripeptide derivatives with three stereogenic centers (±)-G1-G9 have been prepared from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d has been synthesized from d-phenylalanine and (1 S,2 S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (±)-G1-G9 was carried out in the presence of TAMCSAs 1a-1d by 1H NMR spectroscopy. The results indicate that enantiomers of (±)-G1-G9 can be effectively discriminated in the presence of TAMCSAs 1a-1d by 1H NMR signals of multiple protons exhibiting nonequivalent chemical shifts (ΔΔδ) up to 0.616 ppm. Furthermore, enantiomers of (±)-G1-G9 were easily assigned by comparing 1H NMR signals of the split corresponding protons with those attributed to a single enantiomer. Different optical purities (ee up to 90%) of G1 were clearly observed and calculated in the presence of TAMCSAs 1a-1d, respectively. Intermolecular hydrogen bonding interactions were demonstrated through theoretical calculations of enantiomers of (±)-G1 with TAMCSA 1a by means of the hybrid functional theory with the standard basis sets of 3-21G of the Gaussian 03 program." @default.
• W2897518504 created "2018-10-26" @default.
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• W2897518504 date "2018-10-22" @default.
• W2897518504 modified "2023-10-12" @default.
• W2897518504 title "Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from <scp>d</scp>-Phenylalanine and (1<i>S</i>,2<i>S</i>)-(+)-1,2-Diaminocyclohexane via ¹H NMR Spectroscopy" @default.
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• W2897518504 doi "https://doi.org/10.1021/acs.joc.8b02212" @default.
• W2897518504 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6499380" @default.
• W2897518504 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30346768" @default.
• W2897518504 hasPublicationYear "2018" @default.
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