Chemical aspects of penicillin allergy: imidazole-catalysed penicilloylation

Yamana, Tsukinaka; Tsuji, Akira; Miyamoto, Etsuko; Kiya, Emi

doi:10.1111/j.2042-7158.1975.tb10702.x

Cited by 15 publications

(3 citation statements)

References 7 publications

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“…25,26 The ammonium group is particularly important in biotechnology since it constitutes part of many active pharmaceutical compounds. [27][28][29] A recent trend is the co-crystallization of some pharmaceutical compounds with receptors like resorcinarenes and pyrogallarenes with the hope of improving their pharmaceutical properties, 30,31 making crystal engineering 32 a useful tool in analysing supramolecular assemblies. A recent example is the co-crystallization of the pharmaceutical drug gabapentin, a primary amine widely used for the treatment of epilepsy and neuropathic pain, 33,34 with pyrogallarenes, which was studied by Atwood et al 30 Secondary and tertiary ammonium salts possess the hydrogen bond donating groups -NH 2 and -NH, respectively, and these can further enhance their complexation through intermolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

2015

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The binding of different categories of alkyl ammonium (secondary and tertiary mono-and diammonium) salts by resorcinarenes and a pyrogallarene through weak interactions were analysed in all phases. 1 H NMR spectroscopy and electrospray ionisation mass spectrometry were utilized in analysing the complexes in solution and in the gas phase respectively. The 1 H NMR titration studies in methanol-d 4 reveal the association constants for the 1:1 complexes to vary according to the electronic properties of hosts as well as the size, geometric orientation and charge concentration of the guest cations with binding constants of up to 950 M -1 in some cases. Mass spectrometry reveals 1:1 monomeric and 1:2 dimeric complexes in the gas phase. Six co-crystals, three of which are dimeric host-guest capsular assemblies, two open inclusion complexes and a pseudocapsular methanol solvate were analysed in the solid state through single-crystal X-ray diffraction. The crystal structures confirm the complexes to be held together by multiple cation···π, CH···π and hydrogen bond interactions.

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Section: Introductionmentioning

confidence: 99%

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

2015

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“…The ionic strength was adjusted to 0.5 with potassium chloride. The kinetic technique was almost the same as one used previously for penicillin aminolysis (12)(13)(14).…”

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confidence: 87%

Chemical Reactions in Cephalosporin Allergy: High-Pressure Liquid Chromatographic Analysis of Cephalosporin Aminolysis Kinetics

Tsuji

Miyamoto

Yamana

1979

Journal of Pharmaceutical Sciences

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“…Imidazole is known to catalyze hydroxylaminolysis of the @-lactam of penicillins (9). The addition of imidazole to this reaction showed some increase in yield of the 375-nm absorbing species, and the amount of yield increase was only slightly dependent on imidazole concentration over a broad range.…”

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confidence: 95%