The Acidic Dissociation Constants of Phenoxyacetic Acid and its Derivatives

Hayes, Norman V.; Branch, Gerald E. K.

doi:10.1021/ja01248a031

Cited by 56 publications

(24 citation statements)

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“…TAAC exhibited a p K a of 4.1, compared to the reported p K a of 3.23 for the analagous 2-(2-methoxyphenoxy)acetic acid 37. Previous studies of sterically congested acetic acid derivatives have shown p K a differences of similar magnitude, up to 1.5 p K a units 38.…”

Section: Resultsmentioning

confidence: 60%

Substituent Effects on Xenon Binding Affinity and Solution Behavior of Water-Soluble Cryptophanes

et al. 2009

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A water-soluble triacetic acid cryptophane-A derivative (TAAC) was synthesized and determined by isothermal titration calorimetry (ITC) and fluorescence quenching assay to have a xenon association constant of 33,000 M−1 at 293 K, which is the largest value measured for any host molecule to date. Fluorescence lifetime measurements of TAAC in the presence of varying amounts of xenon indicated static quenching by the encapsulated xenon and the presence of a second non-xenon-binding conformer in solution. Acid-base titrations and aqueous NMR spectroscopy of TAAC and a previously synthesized tri-(triazole propionic acid) cryptophane-A derivative (TTPC) showed how solvation of the carboxylate anions can affect the aqueous behavior of the large, nonpolar cryptophane. Specifically, whereas only the crown-crown (CC) conformer of TTPC was observed, a crown-saddle (CS) conformer of TAAC was also detected in aqueous solution.

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Section: Resultsmentioning

confidence: 60%

Substituent Effects on Xenon Binding Affinity and Solution Behavior of Water-Soluble Cryptophanes

et al. 2009

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“…Chemicals were purchased from Sigma-Aldrich and Lancaster Synthesis (Strasbourg, France) and were of analytical grade. Non-commercial compounds in the phenoxyacetic series were prepared from corresponding phenols and chloroacetic acid (Hayes and Branch 1943). The R(+) and S()) enantiomers of IV-2 were separated by crystallization of their diastereoisomer salts with brucine and strychnine (Julia and Tcherno 1957) and those of IV-3 by using HPLC on a chiral permethylated a-cyclodextrin column (NUCLEODEX a-PM; Macherey-Nagel, Hoerdt, France).…”

Section: Methodsmentioning

confidence: 99%

Inhibitors of the carrier-mediated influx of auxin in suspension-cultured tobacco cells

Imhoff

Muller

Guern

et al. 2000

Planta

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Active auxin transport in plant cells is catalyzed by two carriers working in opposite directions at the plasma membrane, the influx and efflux carriers. A role for the efflux carrier in polar auxin transport (PAT) in plants has been shown from studies using phytotropins. Phytotropins have been invaluable in demonstrating that PAT is essential to ensure polarized and coordinated growth and to provide plants with the capacity to respond to environmental stimuli. However, the function of the influx carrier at the whole-plant level is unknown. Our work aims to identify new auxin-transport inhibitors which could be employed to investigate its function. Thirty-five aryl and aryloxyalkylcarboxylic acids were assayed for their ability to perturb the accumulation of 2,4-dichlorophenoxyacetic acid (2,4-D) and naphthalene-1-acetic acid (1-NAA) in suspension-cultured tobacco (Nicotiana tabacum L.) cells. As 2,4-D and 1-NAA are preferentially transported by the influx and efflux carriers, respectively, accumulation experiments utilizing synthetic auxins provide independant information on the activities of both carriers. The majority (60%) of compounds half-inhibited the carrier-mediated influx of [14C]2,4-D at concentrations of less than 10 microM. Most failed to interfere with [3H]NAA efflux, at least in the short term. Even though they increasingly perturbed auxin efflux when given a prolonged treatment, several compounds were much better at discriminating between influx and efflux carrier activities than naphthalene-2-acetic acid which is commonly employed to investigate influx-carrier properties. Structure-activity relationships and factors influencing ligand specificity with regard to auxin carriers are discussed.

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“…The residue was finally dissolbed in water for assay. The met hod of Hayes and Branch (1943) was used for the preparation of radioactive phenoxyacetic acid. [l-1 iC]Monochloroacetic acid (12 mg. 1 niCi).…”

Section: Methodsmentioning

confidence: 99%

Acylation of transfer ribonucleic acid with the N-hydroxysuccinimide ester of phenoxyacetic acid

Friedman¹

1972

Biochemistry

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Uncharged rat liver tRNA can be eluted from BDcellulose columns with 0.8 M sodium chloride, with the exception of tRNAPhe, which can only be eluted with 0.8 M sodium chloride containing ethanol. When the uncharged rat liver tRNA is reacted with the N-hydroxysuccinimide ester of phenoxyacetic acid, there is an increase in the amount of tRNA that is eluted in the presence of ethanol. Greater than 5 0 z of the tRNAs for tyrosine, threonine, isoleucine, cysteine, and asparagine can now be eluted only in the presence of ethanol. Only a small fraction of the tRNA from Escherichin coli and yeast shifted into the ethanol fraction after reac-T here have been several reports of the presence of certain bases in transfer ribonucleic acid that can undergo acylation reactions. However, the nature of these bases has not been fully characterized, nor has it been determined whether these are rare bases, or one or more of the four major bases, that are especially reactive because of their conformation in tRNA. With the advent of BD-cellulose' columns, which have affinity

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The Acidic Dissociation Constants of Phenoxyacetic Acid and its Derivatives

Cited by 56 publications

References 0 publications

Substituent Effects on Xenon Binding Affinity and Solution Behavior of Water-Soluble Cryptophanes

Substituent Effects on Xenon Binding Affinity and Solution Behavior of Water-Soluble Cryptophanes

Inhibitors of the carrier-mediated influx of auxin in suspension-cultured tobacco cells

Acylation of transfer ribonucleic acid with the N-hydroxysuccinimide ester of phenoxyacetic acid

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