Chemistry of cephalosporin antibiotics. XIV. Reaction of cephalosporin C with nitrosyl Chloride

Morin, Robert B.; Jackson, B.; Flynn, Edwin H.; Roeske, Roger W.; Andrews, Sandra L.

doi:10.1021/ja01034a022

Cited by 56 publications

(11 citation statements)

References 2 publications

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“…Newer generation cephalosporins have previously been modified with the removal of the aminoadipoyl sidechain to form 7-aminocephalosporanic acid (Fig. 3), rendering it 100-fold more effective than the older-generation cephalosporin [15][16]. This modification enabled cephalosporin to be less susceptible to hydrolysis by the β-lactamase enzyme [17].…”

Section: Figure 1 Hydrolysis Mechanisms Of Penicillinmentioning

confidence: 99%

Plant-Derived Antimicrobials: Insights into Mitigation of Antimicrobial Resistance

et al. 2018

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Antibiotic resistance had first been reported not long after the discovery of the first antibiotic and has remained a major public health issue ever since. Challenges are constantly encountered during the mitigation process of antibiotic resistance in the clinical setting; especially with the emergence of the formidable superbug, a bacteria with multiple resistance towards different antibiotics; this resulted in the term multidrug resistant (MDR) bacteria. This rapid evolution of the resistance phenomenon has propelled researchers to continuously uncover new antimicrobial agents in a bid to hopefully, downplay the rate of evolution despite a drying pipeline. Recently, there has been a paradigm shift in the mining of potential antimicrobials; in the past, targets for drug discovery were from microorganisms and at current, the focus has moved onto plants, this is mainly due to the beneficial attributes that plants are able to confer over that of microorganisms. This review will briefly discuss antibiotic resistance mechanisms employed by resistant bacteria followed by a detailed expository regarding the use of secondary metabolites from plants as a potential solution to the MDR pathogen. Finally, future prospects recommending enhancements to the usage of plant secondary metabolites to directly target antibiotic resistant pathogens will be discussed.

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Section: Figure 1 Hydrolysis Mechanisms Of Penicillinmentioning

confidence: 99%

Plant-Derived Antimicrobials: Insights into Mitigation of Antimicrobial Resistance

et al. 2018

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“…The first effective method of side chain cleavage made use of the reaction of (179) with nitrosyl chloride (152). Loss of nitrogen from the intermediate diazo compound (181) gives imine (182) which on hydrolysis provides 7-ACA (180) and the lactone (183).…”

Section: References Pp 89-106mentioning

confidence: 99%

“…Conversion to the amino-acid followed by cyclisation to the ~-lactam resulted in (152) having the (S)-stereochemistry in the side chain. This was corrected to the (R)-configuration by an inversion step after conversion to the ~-keto-ester.…”

mentioning

confidence: 99%

Naturally Occurring β-Lactams

Southgate

Elson

1985

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Cephalosporin-C possesses weak antimicrobial activity, but substitutions on C 3 and C 7 positions of its β-lactam ring along with other structures generate semisynthetic cephalosporins with diversified antimicrobial activity, e.g., cefazolin, cefotoxime, cephamandole, cephaclor, and so on. The chemical methods of 7-ACA production are tedious, time consuming and involve multiple costly steps (4,5), and hence, attempts have been made to produce 7-ACA by a biocatalytic process. Cephalosporin acylases are classified in to two groups depending on their substrate specificity: glutaryl 7-ACA acylases (GL-7-ACA acylases), also known as 7-β-(4-carboxybutanamido) cephalosporanic acid acylases (1)(2)(3)(6)(7)(8)(9)(10)(11), which are involved in the threestep conversion of CPC to 7-ACA, and cephalosporin-C acylase (CPC acylase), which have been reported in a single-step conversion (1,2).…”

Section: Introductionmentioning

confidence: 99%

Reusability of entrapped cells of Pseudomonas diminuta for production of 7-aminocephalosporanic acid

Nigam

Kundu

Ghosh

2007

Appl Biochem Biotechnol

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Entrapped cells of P. diminuta were used for the production of 7-aminocephalosporanic acid (7-ACA), a key intermediate required for the production of most of the clinically used cephalosporin derivatives, i.e., semisynthetic cephalosporins. The repeated batch production of 7-ACA with entrapped cells of P. diminuta in different carriers were carried out for six cycles at optimal conditions. It was found that 33% , 38%, and 47% of activity was lost with chitosan, gelatin, and agar, respectively as immobilizing supports after the sixth cycle of operation.

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Chemistry of cephalosporin antibiotics. XIV. Reaction of cephalosporin C with nitrosyl Chloride

Cited by 56 publications

References 2 publications

Plant-Derived Antimicrobials: Insights into Mitigation of Antimicrobial Resistance

Plant-Derived Antimicrobials: Insights into Mitigation of Antimicrobial Resistance

Naturally Occurring β-Lactams

Reusability of entrapped cells of Pseudomonas diminuta for production of 7-aminocephalosporanic acid

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