(S) 2-phenyl-2-(p-tolylsulfonylamino)acetic acid. Structure, acidity and its alkali carboxylates

Duarte-Hernández, Angélica M.; Contreras, Rosalinda; Suárez-Moreno, Galdina V.; Montes-Tolentino, Pedro; Ramos-Garcı́a, Iris; González, Felipe J.; Flores‐Parra, Angelina

doi:10.1016/j.molstruc.2014.11.057

Cited by 5 publications

(3 citation statements)

References 37 publications

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“…The absolute configuration of the a -arylglycines were determined via crystal structure of compound 25a. The crystal data are equivalent to the according literature ( Duarte-Hernández et al, 2015 ).…”

Section: Methodsmentioning

confidence: 99%

Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of α-arylglycine derivatives

Jakob¹,

Diehl²,

Horst³

et al. 2023

Front. Chem.

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A palladium-catalyzed asymmetric three-component synthesis of α-arylglycine derivatives starting from glyoxylic acid, sulfonamides and arylboronic acids is reported. This novel, operationally simple method offers access to the α-arylglycine scaffold in good yields and enantioselectivities. The utilization of α tailored catalyst system enables the enantioselective synthesis of the desired α-arylglycines despite a fast racemic background reaction. The obtained products can be directly employed as building blocks in peptide synthesis.

show abstract

Section: Methodsmentioning

confidence: 99%

Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of α-arylglycine derivatives

Jakob¹,

Diehl²,

Horst³

et al. 2023

Front. Chem.

View full text Add to dashboard Cite

show abstract

“…The absolute configuration of the α-arylglycines were determined via crystal structure of compound 25a. The crystal data are equivalent to the according literature (Duarte-Hernández et al 2015).…”

Section: Absolute Configurationmentioning

confidence: 99%

Palladium-Catalyzed Asymmetric Three-Component Reaction between Glyoxylic Acid, Sulfonamides and Arylboronic Acids for the Synthesis of alpha-Arylglycine Derivatives

Jakob

Diehl

Horst

et al. 2023

Preprint

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A palladium-catalyzed asymmetric three-component synthesis of alpha-arylglycine derivatives starting from glyoxylic acid, sulfonamides and arylboronic acids is reported. This novel, operationally simple method offers access to the alpha-arylglycine scaffold in good yields and enantioselectivities. The utilization of a tailored catalyst system enables the enantioselective synthesis of the desired alpha-arylglycines despite a fast racemic background reaction. The obtained products can be directly employed as building blocks in peptide synthesis.

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“…Acid–base and other physicochemical properties of various sulfonamides were studied by CE [40–43]. Alternatively, p K a values of sulfonamides were determined by potentiometric titration [44], UV‐Vis spectrophotometry [45], LC [46], cyclic voltammetry [47], or they were theoretically calculated [45, 48].…”

Section: Introductionmentioning

confidence: 99%

Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane‐based inhibitors of carbonic anhydrases by capillary electrophoresis

et al. 2021

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Capillary electrophoresis (CE) has been applied for determination of the thermodynamic acidity constants (pKa) of the sulfamidoalkyl and sulfonamidoalkyl groups, the actual and limiting ionic mobilities and hydrodynamic radii of important compounds, eight carborane‐based inhibitors of carbonic anhydrases, which are potential new anticancer drugs. Two types of carboranes were investigated, (i) icosahedral cobalt bis(dicarbollide)(1‐) ion with sulfamidoalkyl moieties, and (ii) 7,8‐nido‐dicarbaundecaborate with sulfonamidoalkyl side chains. First, the mixed acidity constants, pKamix, of the sulfamidoalkyl and sulfonamidoalkyl groups of the above carboranes and their actual ionic mobilities were determined by nonlinear regression analysis of the pH dependences of their effective electrophoretic mobility measured by capillary electrophoresis in the pH range 8.00−12.25, at constant ionic strength (25 mM), and constant temperature (25°C). Second, the pKamix were recalculated to the thermodynamic pKas using the Debye–Hückel theory. The sulfamidoalkyl and sulfonamidoalkyl groups were found to be very weakly acidic with the pKas in the range 10.78−11.45 depending on the type of carborane cluster and on the position and length of the alkyl chain on the carborane scaffold. These pKas were in a good agreement with the pKas (10.67−11.27) obtained by new program AnglerFish (freeware at https://echmet.natur.cuni.cz), which provides thermodynamic pKas and limiting ionic mobilities directly from the raw CE data. The absolute values of the limiting ionic mobilities of univalent and divalent carborane anions were in the range 18.3−27.8 TU (Tiselius unit, 1 × 10−9 m2/Vs), and 36.4−45.9 TU, respectively. The Stokes hydrodynamic radii of univalent and divalent carborane anions varied in the range 0.34−0.52 and 0.42−0.52 nm, respectively.

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(S) 2-phenyl-2-(p-tolylsulfonylamino)acetic acid. Structure, acidity and its alkali carboxylates

Cited by 5 publications

References 37 publications

Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of α-arylglycine derivatives

Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of α-arylglycine derivatives

Palladium-Catalyzed Asymmetric Three-Component Reaction between Glyoxylic Acid, Sulfonamides and Arylboronic Acids for the Synthesis of alpha-Arylglycine Derivatives

Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane‐based inhibitors of carbonic anhydrases by capillary electrophoresis

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