Chemistry of cephalosporin antibiotics. XV. Transformations of penicillin sulfoxide. Synthesis of cephalosporin compounds

Morin, Robert B.; Jackson, B.; Mueller, Richard A.; Lavagnino, E. R.; Scanlon, W. B.; Andrews, Sandra L.

doi:10.1021/ja01034a023

Cited by 179 publications

(52 citation statements)

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“…Cycloheximide, kanamycin, and streptomycin are also reported to inhibit the protein synthesis, but they do not inhibit the growth of Gram-positive bacteria (Madigan et al, 2000). Cephalexin and cycloserine inhibit the cell wall synthesis, and mitomycin C inhibits DNA synthesis (Iyer and Szybalski, 1964;Morin et al, 1969;Neuhaus and Lynch, 1964). As mentioned above, antibiotics influence biosyntheses, and induced the cystite formation of A. ureafaciens NRIC 0157 T .…”

Section: Discussionmentioning

confidence: 94%

The formation and structures of cystites of Arthrobacter ureafaciens NRIC 0157T induced by antibiotics.

Tanaka

Uchimura

Komagata

2001

J. Gen. Appl. Microbiol.

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The cystite formation of Arthrobacter ureafaciens NRIC 0157 T was induced by some antibiotics, and the addition of tetracycline at a lag phase was effective for cystite formation in YPM liquid medium. Cystites differed from vegetative cells in the cell wall structure, protein content, and water content. Furthermore, the characteristics and structures of cystites induced by tetracycline were similar to those of cystites produced by nutritional imbalance in CT medium. Consequently, various triggers would induce cystite formation. It is interesting that cystite formation was found in part of the Arthrobacter strains and seemed to correlate with the type of peptidoglycan.Key Words--Arthrobacter; Arthrobacter ureafaciens; cell wall; cystites J. Gen. Appl. Microbiol., 47, 85-97 (2001) * Address reprint requests to: Dr. Naoto Tanaka, Laboratory of General and Applied Microbiology, Department of Applied Biology and Chemistry, Faculty of Applied Bioscience, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan. E-mail: QWP07736@nifty.ne.jp T : Indicates the type strain of a species. Full PaperThis paper deals with the effect of antibiotics on the cystite formation of A. ureafaciens NRIC 0157T and the structures of cell walls and the intracellular structures of cystites and vegetative cells. A correlation between the imbalance growth and the cystite formation of A. ureafaciens NRIC 0157 T is discussed. Materials and MethodsBacterial strains. The following strains were used in this study: (Tanaka et al., 2000), and was composed of 1.0% beef extract (Difco Laboratories), 1.0% peptone (Mikuni Kagaku Sangyo Ltd.), 0.5% NaCl, and 1.5% agar. The pH was adjusted to 7.0 with NaOH.Cultivation. Strains were aerobically precultured in YPM liquid medium with 30 ml L-form test tubes or 500 ml Erlenmeyer flasks at 28 or 37°C. Cells at a late logarithmic phase were collected by centrifugation at 1,600ϫg for 10 min at 20°C and washed twice with saline. The washed cells were suspended in saline, and the suspension was inoculated with 1% (v/v) into fresh YPM liquid medium, CT liquid medium, or other liquid media with a pipette. The liquid media were aerobically incubated at 28 or 37°C for 1 or 2 days up to full growth.Determination of bacterial growth. Bacterial growth in liquid media was determined by absorbance at 660 nm with a single-beam spectrophotometer (NO-VASPEC II, Amersham Pharmacia Biotech, Tokyo, Japan).Investigation of cell shapes. Cell shapes were investigated with a phase-contrast microscope (BX-50, oil immersion lens, Olympus, Tokyo, Japan). The change of cell shapes was monitored at various intervals during the growth.Determination of the Gram reaction by the KOH reaction. An incubated liquid medium was centrifuged at 1,600ϫg for 10 min, and precipitates were used to detect the KOH reaction (Powers, 1995).Cell counts. A total cell number was determined with a Thoma-Zeiss counting chamber, and a viable cell number was determined by the number of colonies appearing on nutrient agar plates...

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Section: Discussionmentioning

confidence: 94%

The formation and structures of cystites of Arthrobacter ureafaciens NRIC 0157T induced by antibiotics.

Tanaka

Uchimura

Komagata

2001

J. Gen. Appl. Microbiol.

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“…This trend is seen in the solid state (14), and is reflected (15,16) in the different p-lactam carbonyl stretching frequencies of these compounds (15: 1790 cm-';…”

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confidence: 81%

Sulfur-free penicillin derivatives. VII. Multiple functionalization of 2-azetidinyl-3-methyl-2-butenoates

Wolfe¹,

Shaw²

1982

Can. J. Chem.

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SAUL WOLFE and CHIA-CHENG SHAW. Can. J. Chem. 60, 144 (1982). The title compounds, substituted with chlorine in the 4'-position and with phthalimido, 2,2,2-trichloroethoxycarbonylamino, or phenoxycarbonylamino in the 3'-position of the azetidinone ring, have been converted to bis-allylic formates via bromination of both methyl groups with excess N-bromosuccinimide, and displacement of both bromines by formate ions in methylene chloride solvent. The diformates react smoothly with a deficit of a boron halide to form EIZ mixtures of halogeno-formates, in which the E-isomer predominates. Depending on the 3'-azetidinyl substituent, these halogeno-formates undergo a second displacement with acetate either with retention of olefinic geometry or inversion of olefinic geometry. The mechanisms of these reactions are discussed, along with further transformations leading to hydroxylactones, halogenolactones, halogenohydrins, and other compounds. Examination of the proton magnetic resonance spectra of twenty-one compounds reveals that methylene protons cis to the p-lactam nitrogen atom of a methyl 2-azetidinyl-2-butenoate are found at higher field than methylene protons cis to the methoxycarbonyl group. This observation appears to provide a more reliable criterion for the assignment of configuration to geometrical isomers than one based on the magnitude of the chemical shift nonequivalence of the E and Z methylene protons.SAUL WOLFE et CHIA-CHENG SHAW. Can. J. Chem. 60, 144 (1982). Le compose mentionne dans le titre portant une chlore en position 4' et un groupe phtalimido, trichloro-2,2,2 ethoxycarbonylamino ou phenoxycarbonylamino en position 3' du cycle azetidinone, soumis a une bromation des groupes methyles au moyen d'un exces de N-bromosuccinimide suivie par deplacement des bromes par des ions formiates dans le chlorurc de methyli-ne, conduit aux formiates his-allyliques. Les diformiates reagissent avec un defaut d'halogenure de bore en donnant les melanges EIZ d'halogenofonniates dans lesquels I'isomere E est majoritaire. Dkpendant du substituant en position 3' du cycle azetidinyle, ces halogenoformiates, en presence d'un acetate, subissent une deuxieme reaction de deplacernent avec retention ou inversion de la geometrie de I'olefine. On discute des rnecanismes de ces reactions ainsi que des transformation plus poussees qui conduisent a des hydroxylactones, des halogenolactones, des halohydrines et a d'autres composes. Les spectres de rmn du IH de vingt et un composes revelent que les protons methyleniques en position 6 par rapport a I'atome d'azote du p-lactame du azetidinyl-2 butene-2 oate de methyle, sont deplaces vers les champs forts par rapport aux protons methyleniques en position cis du groupe methoxycarbonyle. Ces observations semblent fournir des criteres plus surs, que ceux fondes sur I'ordre de grandeur de la non equivalence des deplacements chimiques des protons mtthyliques des isomeres E et Z, pour determiner la configuration des isomeres geometriques.[Traduit par le journal]The first synthesis of a 1-ox...

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“…It was proposed that this transformation was mechanistically analogous to the Morin rearrangement of penams to cephams. 42 In fact, it had been hoped that the presumed intermediate N-acyliminium ion 91 might initiate the double cyclization sequence outlined in Scheme 14, but this was not the case; 92 was a dead end as studies with CF 3 CO 2 D indicated that it was not protonated to give 91. It is also notable that isomers 97 and 98 are in equilibrium under the reaction conditions.…”

Section: Scheme 14mentioning

confidence: 99%

The spiroquinazoline family of alkaloids: a review

Hart¹

2010

Arkivoc

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Chemistry of cephalosporin antibiotics. XV. Transformations of penicillin sulfoxide. Synthesis of cephalosporin compounds

Cited by 179 publications

References 3 publications

The formation and structures of cystites of Arthrobacter ureafaciens NRIC 0157T induced by antibiotics.

The formation and structures of cystites of Arthrobacter ureafaciens NRIC 0157T induced by antibiotics.

Sulfur-free penicillin derivatives. VII. Multiple functionalization of 2-azetidinyl-3-methyl-2-butenoates

The spiroquinazoline family of alkaloids: a review

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