Amino Acid Ligand Chirality for Enantioselective Syntheses

Micskei, Károly; Patonay, Tamás; Caglioti, Luciano; Pályi, Gyula

doi:10.1002/cbdv.200900325

Cited by 45 publications

(17 citation statements)

References 82 publications

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“…[1][2][3] They also serve as important synthons andc hirality sourcesf or diversef unctional organic molecules. [4,5] In recent years, the development of fluorescent molecular probes to discriminate the enantiomerso fa minoa cids hasr eceived significant attention. [6,7] The use of fluorescence in chiral recognition not only provides rapid analysis of the chiral composition of the substrates, [8] but maya lso allow direct imagingo ft he enantiomers of amino acids in cells.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Determination of Concentration and Enantiomeric Composition of Amino Acids in Aqueous Solution by Using a Tetrabromobinaphthyl Dialdehyde Probe

Iqbal

Sheng

Jiang

et al. 2019

Chemistry A European J

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3,3'-Diformyl-1,1'-bi-2-naphthol or its methoxymethyl-protected derivative is found to undergo ah ighly selective reactionw ith excess bromine in CH 2 Cl 2 at reflux to give the novel 5,5',6,6'-tetrabrominatedp roduct (S)-or (R)-2. The observed electrophilics ubstitution at the 5,5'-positons of an optically active binaphthyl compound is unprecedented. Unlike unbrominated 3,3'-diformyl-1,1'-bi-2-naphthol, which is not suitable for fluorescent recognition in water, compound (S)-2,i nc ombination with Zn 2 + ,e xhibits ah ighly enantioselective fluorescent response toward amino acids in aqueouss olution (HEPES buffer,p H7.4). It is furtherf ound that the condensationp roduct of (R)-2 with tryptophan,( R)-3,s hows dual-responsive emissions toward amino acids;t he short wavelength (l 1 = 350 nm) emission is sensitivet ot he concentration of the substrate regardless of the chiral configuration and the long wavelength (l 2 > 500 nm) emission is highlye nantioselective. Thus,t he use of (R)-3 allowst he simultaneousdetermination of the concentration and enantiomeric composition of an amino acid sample from one fluorescence measurement.[a] S. Iqbal, Dr.

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Section: Introductionmentioning

confidence: 99%

Simultaneous Determination of Concentration and Enantiomeric Composition of Amino Acids in Aqueous Solution by Using a Tetrabromobinaphthyl Dialdehyde Probe

Iqbal

Sheng

Jiang

et al. 2019

Chemistry A European J

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“…It is known that the structure of α‐amino acids as ligands can accelerate metal‐catalyzed reactions . Ma et al .…”

Section: Introductionmentioning

confidence: 99%

Methionine: a green and efficient promoter for copper‐catalyzed Sonogashira cross‐coupling reactions

Hajipour

Mohammadsaleh

2015

Applied Organom Chemis

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aIn the presence of amino acids as environmentally friendly ligands, CuI-catalyzed Sonogashira cross-coupling of various aryl halides with phenylacetylene was conducted to afford the corresponding internal alkynes. L-Methionine was found to be useful for this palladium-free and amine-free coupling reaction. It was also found that the solvent system plays an important role in this reaction, and significantly affects the product formation and reaction rate. Sonogashira coupling of aryl iodides and aryl bromides in dimethylsulfoxide or dimethylformamide gave the coupled products in good to excellent yields.

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“…On the basis of this experience we tested the reduction of α-oximino carboxylic acids, which are direct precursors of the (natural) α-amino acids (Fig. 11) [134,135].…”

Section: Toward Designed Soai-type Systems?mentioning

confidence: 99%

Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis

et al. 2015

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Absolute asymmetric synthesis (AAS) is the preparation of pure (or excess of one) enantiomer of a chiral compound from achiral precursor(s) by a chemical reaction, without enantiopure chiral additive and/or without applied asymmetric physical field. Only one well-characterized example of AAS is known today: the Soai-autocatalysis. In an attempt at clarification of the mechanism of this particular reaction we have undertaken empirical and stochastic analysis of several parallel AAS experiments. Our results show that the initial steps of the reaction might be controlled by simple normal distribution ("coin tossing") formalism. Advanced stages of the reaction, however, appear to be of a more complicated nature. Symmetric beta distribution formalism could not be brought into correspondence with the experimental observations. A bimodal beta distribution algorithm provided suitable agreement with the experimental data. The parameters of this bimodal beta function were determined by a Pólya-urn experiment (simulated by computer). Interestingly, parameters of the resulting bimodal beta function give a golden section ratio. These results show, that in this highly interesting autocatalysis two or even perhaps three catalytic cycles are cooperating. An attempt at constructing a "designed" Soai-type reaction system has also been made.

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Amino Acid Ligand Chirality for Enantioselective Syntheses

Cited by 45 publications

References 82 publications

Simultaneous Determination of Concentration and Enantiomeric Composition of Amino Acids in Aqueous Solution by Using a Tetrabromobinaphthyl Dialdehyde Probe

Simultaneous Determination of Concentration and Enantiomeric Composition of Amino Acids in Aqueous Solution by Using a Tetrabromobinaphthyl Dialdehyde Probe

Methionine: a green and efficient promoter for copper‐catalyzed Sonogashira cross‐coupling reactions

Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis

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