Recent chemistry of the β-lactam antibiotics

Sammes, Peter G.

doi:10.1021/cr60299a003

Cited by 136 publications

(31 citation statements)

References 106 publications

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“…In alkaline conditions, penicilloic acid is known to be a major product, but it undergoes decarboxylation into penilloic acid [37][38][39]. While the molecule is most stable between pH 5 and 8, spontaneous fission and rearrangement of the β-lactam ring into an oxazolone ring and simultaneous cleavage of the thiazolidine ring may occur, resulting in penicillenic acid [40]. Due to stability issues in aqueous media, penicillin G should be kept in buffered solutions such as phosphate, acetate, or citrate, of which citrate buffer at pH 7 is the most effective at preventing degradation [41].…”

Section: Penicillin G and Its Metabolitesmentioning

confidence: 99%

Penicillin G's function, metabolites, allergy, and resistance.

Canzani¹,

Aldeek²

2017

nutrition-human-health

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The discovery of penicillin G was one of the most significant findings of the 20 th century and certainly one of the most important discoveries in modern medicine. Since the 1940s, the world has remained dependent on this safe and effective antibiotic, and it has been used extensively not only in human medical applications, but in animal and agriculture to enhance the growth of livestock. Such diverse applications have resulted in the global distribution of this antibiotic, and its dispersal into a wide array of environments. Moreover, penicillin G is known to degrade into immunogenic metabolites, which have been identified in various agricultural products and wastewater systems, fuelling much debate on the safety of the use of this antibiotic. Unfortunately, the overuse of penicillin G and other antibiotics has led to the rise of resistant organisms and ushered us into a new age of treating infectious disease. The rise in resistance associated with penicillin G and its ability to produce allergy inducing metabolites in animal and medicinal applications are deeply intertwined, creating a unique and complex set of public health issues which is the subject of this review. Penicillin G will likely be used for many years to come, thus new understanding and insight is needed to address these public health issues. AbstractPenicillin G's function, metabolites, allergy, and resistance.

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Section: Penicillin G and Its Metabolitesmentioning

confidence: 99%

Penicillin G's function, metabolites, allergy, and resistance.

Canzani¹,

Aldeek²

2017

nutrition-human-health

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“…A solution of the residue in benzene was treated with fuller's earth and charcoal and concentrated to give syrupy crude [0.271 g, 55%; tlc benzene/ethyl acetate (1:1) almost homogeneous] or crystalline benzothiazole 2a (0.140 g, 28%), mp 132.5° (from anhydrous ethanol/hexane), identical (mp, tlc, ir) with an authentic [30] compound. 8, [1,3]benzothiazol-10(5aH)-one 5-Oxide (4) and 6-(2-Benzothiazolyl)-2,3-dimethoxybenzoic Acid (5).…”

Section: Procedures Bmentioning

confidence: 99%

“…condensates of 2-aminothiophenol with aldoses, type 1a,b) are especially unstable in protic solvents and their oxidation by air result in 2aminophenyl disulfides and aldoses [7] as a consequence of a C B A transformation (see Scheme 1). During the second half of the last century, stimulated mainly by the penam cephem ring-expansion transformations of lactam antibiotics [8] containing cyclic N,Sacetal moieties, the chemistry of sulfoxides [9] has been very intensively elaborated. Although the hydrogen peroxide oxidation has been used for the transformation of 3-acylthiazolidines into both the corresponding sulfoxides and sulfones [10], the reactions are time-consuming and often not chemoselective.…”

mentioning

confidence: 99%

Synthesis, oxidation and dehydrogenation of cyclicN,O- andN,S-Acetals. II . Transformation ofN,S-acetals: 3-Acylbenzothiazolines and -thiazolidines

Somogyi

2006

Journal of Heterocyclic Chemistry

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The dehydrogenations with iron(III) chloride, potassium permanganate, and for the first time, CAN, tris‐[trinitrato‐cerium(IV)]‐paraperiodate (TTNCPP), and (diacetoxyiodo)benzene (IBDA) are investigated. Hydrogen peroxide, sodium periodate, potassium permanganate, and ammonium cerium(IV) nitrate (CAN) oxidation of chiral benzothiazolines, O‐ and O,N‐acylated derivatives of the condensates of D‐galactose with 2‐aminothiophenols or L‐cysteine, are also reported.

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“…La synthkse de ces composCs bicycliques a Ct C Cgalement effectuCe par rCaction de cycloaddition [2+ 21 partir de 6H-thiazines-l,3 2 non substituCes en position 2 et comportant en position 4 un groupement fonctionnel Clectroattracteur (3). Les synthkses de composCs P-lactamiques par action des cttknes sur la fonction imine de composCs 1inCaires ou cycliques ont fait l'objet de nombreuses publications (4). Toutefois, peu de travaux concement les 6H-thiazines-1,3 substituCes en positions 2, 4 et 5.…”

Section: Introductionunclassified