Epithienamycins-novel .BETA.-lactams related to thienamycin I. Production and antibacterial activity.

Stapley, E. O.; Cassidy, Patrick J.; Tunac, J. B.; Monaghan, Richard L.; Jackson, M.; Hernandez, Sebastian; Zimmerman, Sheldon B.; Mata, J. M.; Currie, Sara A.

doi:10.7164/antibiotics.34.628

Cited by 42 publications

(6 citation statements)

References 17 publications

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“…Our results and those of earlier workers (6,11) suggest that carbapenem antibiotics and, in addition, penem antibiotics have a common property: they are susceptible to hydrolysis by renal dipeptidase. This property presumably causes a discrepancy between in vitro and in vivo activities and reduces the urinary recovery of these drugs.…”

supporting

confidence: 85%

“…Some of these antibiotics include carbapenem antibiotics such as thienamycin (5), epithienamycins (11), olivanic acids (1), , carpetimycins (9), and asparenomycins (6). Recently, it was found that thienamycin, N-formimidoyl thienamycin (7,14), and related carbapenem compounds were considerably inactivated in vivo by renal dipeptidase (dehydropeptidase-I, EC3.4.14.11) (H. Kropp 272,1980).…”

mentioning

confidence: 99%

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Comparative Stability of Newly Introduced β-Lactam Antibiotics to Renal Dipeptidase

Mikami

Ogashiwa

Saino

et al. 1982

Antimicrob Agents Chemother

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supporting

confidence: 85%

mentioning

confidence: 99%

Comparative Stability of Newly Introduced β-Lactam Antibiotics to Renal Dipeptidase

Mikami

Ogashiwa

Saino

et al. 1982

Antimicrob Agents Chemother

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“…564 Since thienamycin fermentation has been reported to require cobalt, 523 it was proposed 564 that the two sequential methyl-transfers probably take place from 5-methyltetrahydrofolate, by a B 12 -dependent synthase, analogous to the biosynthesis of methionine from 5-methyltetrahydrofolate, which also proceeds with net retention of conguration. [570][571][572][573] Vitamin B 12 has been reported to be excreted from a blocked mutant that does not produce thienamycin, and also to restore the thienamycin producing capacity to other blocked mutants. 574 It is also noteworthy that methylmalonyl-CoA mutase, which interconverts (2R)-methylmalonyl-CoA and succinyl-CoA, is a vitamin B 12 dependent enzyme; [575][576][577] the dependence of thienamycin biosynthesis on cobalt/vitamin B 12 may imply that methylmalonyl-CoA is a potential in vivo substrate.…”

Section: Thienamycin Biosynthesismentioning

confidence: 99%

“…Thienamycin was also isolated from S. penemijaciens 729. epi-Thienamycins A-F were isolated from S. flavogriseus571,730 and from S. olivaceus 572,[731][732][733][734][735]. The olivanic acids MM 4550572,733,734 and MM 27696736 were isolated from S. olivaceus.…”

mentioning

confidence: 99%

The enzymes of β-lactam biosynthesis

et al. 2013

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The β-lactam antibiotics and related β-lactamase inhibitors are amongst the most important small molecules in clinical use. Most, but not all, β-lactams including penicillins, cephalosporins, and clavulanic acid are produced via fermentation or via modification of fermented intermediates, with important exceptions being the carbapenems and aztreonam. The desire for more efficient routes to existing antibiotics and for access to new and synthetically challenging ones stimulates continued interest in β-lactam biosynthesis. We review knowledge of the pathways leading to β-lactam antibiotics focusing on the mechanisms, structures and biocatalytic applications of the enzymes involved.

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“…In addition, the IPNS proteins from S. clavuligerus and S. cattleya, which are responsible for the formation of cephamycin C b-lactam ring, also cluster together based on the similarities of their amino-acid sequences, but the evolutionary significance of this observation is not clear at this point (Figure 2b). Interestingly, inspection of the published genome sequence for Streptomyces flavogriseus, previously reported as an epi-thienamycin producer, 60 shows that it carries both a thienamycin-type carbapenem gene cluster and a complete clavulanic acid gene cluster 7 but no penicillin/cephalosporin cluster, showing yet a different combination Figure 2b. Accession numbers for the Bls, Cps and TblS sequences used are listed in Table 1.…”

Section: The Carbapenem Groupmentioning

confidence: 99%

Origins of the β-lactam rings in natural products

Tahlan

Jensen

2013

J Antibiot

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Naturally occurring β-lactam compounds fall into four basic structural groups, the penicillins/cephalosporins, the clavams, the carbapenems and the monocyclic β-lactams. Biosynthetic studies have clarified the steps involved in the formation of the β-lactam ring for the first three of these groups, but the corresponding process or processes for the monocyclic β-lactams remains obscure. Isopenicillin N synthase is responsible for formation of the β-lactam ring in all penicillin/cephalosporin compounds, and the reaction catalyzed is completely separate from that of β-lactam synthetase, the enzyme responsible for ring formation in all clavam compounds. Conversely, carbapenam synthetase, the enzyme responsible for β-lactam ring formation for all carbapenem compounds, shows clear relatedness to β-lactam synthetase, despite differences in the substrates and the products for the two enzymes. The mechanism of ring formation has not yet been clarified for any of the monocyclic β-lactams, but a third distinct mechanism of β-lactam ring formation seems likely, and this group includes such a diverse collection of structures that even more new ring-forming reactions may be involved.

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Epithienamycins-novel .BETA.-lactams related to thienamycin I. Production and antibacterial activity.

Cited by 42 publications

References 17 publications

Comparative Stability of Newly Introduced β-Lactam Antibiotics to Renal Dipeptidase

Comparative Stability of Newly Introduced β-Lactam Antibiotics to Renal Dipeptidase

The enzymes of β-lactam biosynthesis

Origins of the β-lactam rings in natural products

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