Synthesis, resolution, and determination of absolute configuration of protected α-ethynylphenylalanine enantiomers

Benfodda, Zohra; Bénimèlis, David; Jean, Marion; Naubron, Jean-Valère; Rolland, Valérie; Meffre, Patrick

doi:10.1007/s00726-015-1917-1

Cited by 6 publications

(3 citation statements)

References 57 publications

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“…The development of stereoselective synthetic procedures for amino acid analogs is also intricately tied to the need for reliable and precise methods of chiral analysis [ 30 , 31 , 32 , 33 ].…”

Section: Discussionmentioning

confidence: 99%

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

Aiello,

Recchimurzo,

Balzano

et al. 2024

Molecules

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In the exploration of chiral solvating agents (CSAs) for nuclear magnetic resonance (NMR) spectroscopy designed for the chiral analysis of amino acid derivatives, notable advancements have been made with thiourea–CSAs. 1-TU, derived from 2-[(1R)-1-aminoethyl]phenol and benzoyl isothiocyanate, is effective in the enantiodifferentiation of N-3,5-dinitrobenzoyl (N-DNB) amino acids. In order to broaden the application of 1-TU for configurational assignment, enantiomerically enriched N-DNB amino acids were analyzed via NMR. A robust correlation was established between the relative position of specific 1H and 13C NMR resonances of the enantiomers in the presence of 1-TU. 1,4-Diazabicyclo[2.2.2]octane (DABCO) was selected for the complete solubilization of amino acid substrates. Notably, the para and ortho protons of the N-DNB moiety displayed higher frequency shifts for the (R)-enantiomers as opposed to the (S)-enantiomers. This trend was consistently observed in the 13C NMR spectra for quaternary carbons bonded to NO2 groups. Conversely, an inverse correlation was noted for quaternary carbon resonances of the carboxyl moiety, amide carbonyl, and methine carbon at the chiral center. This observed trend aligns with the interaction mechanism previously reported for the same chiral auxiliary. The configurational correlation can be effectively exploited under conditions of high dilution or, significantly, under sub-stoichiometric conditions.

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Section: Discussionmentioning

confidence: 99%

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

Aiello,

Recchimurzo,

Balzano

et al. 2024

Molecules

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“…For instance, baseline 15 separation of azelnidipine (compound 4 in Fig.1) was achieved in mobile phase n-hexane/2-propanol (90/10) (DC =3.56) on Chiralpak AD (amylose tris(3,5-dimethylphenylcarbamate)) [57]. The separation factor of chiral oxaliplatin (compound 5 in Fig.1) decreased with the enhancement of the polarity of the mobile phase which even reached 1 on Chiralpak IC [58].…”

Section: Structure Analysismentioning

confidence: 97%

“…Although many chiral compounds can be separated by HPLC effectively [13,14], the absolute configurations of the isomers cannot be confirmed directly [15]. e.g.…”

Section: Introductionmentioning

confidence: 99%

Interactions between pyrazole derived enantiomers and Chiralcel OJ: Prediction of enantiomer absolute configurations and elution order by molecular dynamics simulations

Huang

Luo

et al. 2016

Journal of Molecular Graphics and Modelling

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Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

et al. 2020

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Three N‐Boc‐protected amino acids, l‐serine, l‐aspartic, and l‐glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann‐Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu‐catalyzed click reaction provided a library of amino acid based triazoles, which were further N‐methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).

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Synthesis, resolution, and determination of absolute configuration of protected α-ethynylphenylalanine enantiomers

Cited by 6 publications

References 57 publications

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

Interactions between pyrazole derived enantiomers and Chiralcel OJ: Prediction of enantiomer absolute configurations and elution order by molecular dynamics simulations

Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

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