The Structure of Terramycin<sup>1,2</sup>

Hochstein, F. A.; Stephens, Charles R.; Conover, L. H.; Regna, Peter P.; Pasternack, Robert F.; Gordon, P. N.; Pilgrim, F. J.; Brunings, K. J.; Woodward, R. B.

doi:10.1021/ja01118a001

Cited by 164 publications

(33 citation statements)

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“…Reference substances of OTC, EOTC, ~-APOTC, fl-APOTC, ETC.HC1 and TC.HC1 are available from Acros Organics. AOTC and TL reference substances were prepared in the laboratory according to existing methods [6]. Stock solutions of reference substances were prepared in HC1 0.01 M (OTC, EOTC, ETC and TC) or NH4OH 0.01 M (~-APOTC, fl-APOTC, AOTC, TL).…”

Section: Reagents and Samplesmentioning

confidence: 99%

“…It is unstable in aqueous solution and rearranges to form ~-and /?-apooxytetracycline (~-and/?-APOTC) [6]. These can in turn react to form terrinolide (TL) [6]. Because AOTC, ~-APOTC, /?-APOTC and TL are formed by manufacturing OTC as the hydrochloride salt, these impurities are not present in OTC base.…”

Section: Introductionmentioning

confidence: 96%

“…Anhydrooxytetracycline (AOTC) is formed in acidic medium by degradation at the C-6 hydroxy group. It is unstable in aqueous solution and rearranges to form ~-and /?-apooxytetracycline (~-and/?-APOTC) [6]. These can in turn react to form terrinolide (TL) [6].…”

Section: Introductionmentioning

confidence: 98%

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Development and validation of an improved liquid chromatographic method for the analysis of oxytetracycline

et al. 2002

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SummaryAn improved LC method is described for the separation of oxytetracychne and its impurities. The separation is much better than that obtained with official pharmacopoeia methods. The method uses XTerra RP-18, 5 I~m (25 cm • 4.6 mm I.D.), a silica-based stationary phase with methyl end-capping, claimed to reduce silanol activity. The column temperature is set at 30 ~ and a UV detection is performed at 280 nm. Mobile phase containing acetonitrile -0.25 M tetrabutylammonium hydrogen sulfate pH Z5 -0.25 M ethylenediaminetetraacetic acid pH Z5 -water (115:360:160:365, v/v/v/v) is used at a flow rate of 1.0 mL.min 1, to separate the impurities present in oxytetracychne base.A central composite experimental design is used to optimize the separation. A second isocratic method with higher content of acetonitrile is needed to separate the more retained impurities present only in oxytetracychne hydrochloride. The method is robust and shows good selectivity, repeatability, hnearity and sensitivity.

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Section: Reagents and Samplesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

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Development and validation of an improved liquid chromatographic method for the analysis of oxytetracycline

et al. 2002

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“…(6). DIAOTC was prepared by the addition of acetic anhydride to a solution of OTCO in anhydrous dioxane (23). The 1:l tetracycline urea adduct was precipitated from a saturated aqueous solution of urea by the addition of tetracycline hexahydrate (24).…”

Section: Methodsmentioning

confidence: 99%

A nitrogen-15 nuclear magnetic resonance study of the tetracycline antibiotics

Curtis¹,

Wasylishen²

1991

Can. J. Chem.

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. Can. J. Chem. 69, 834 (1991).Natural abundance I5N NMR has been used to study several tetracycline antibiotics in the solid state and in solution. In the solid state, the I5N chemical shifts of the tetracycline free bases are sensitive to the site of protonation in the "A" ring. A high frequency shift of 14ppm is observed for the keto form of oxytetracycline (N protonated) relative to the en01 form of oxytetracycline (0 protonated). Comparison of I5N chemical shifts in the solid and solution states indicates for the first time that the structural integrity (site of protonation and hence conformation) of the tetracyclines is maintained in (CD,)'SO solutions. In addition, the solid state 15N CP/MAS NMR spectra are sensitive to subtle conformational changes of the "A" ring amide substituent.Key words: antibiotics, tetracyclines, "N NMR, molecular structure RONALD D. CURTIS et RODERICK E. WASYLISHEN. Can. J. Chem. 69, 834 (1991).On a ufilist a RMN du "N en abondance naturelle pour Ctudier plusieurs tCtracycline antibiotiques, a 1'Ctat solid6 et en solution. A I'Ctat solide, les dkplacernents chimiques du "N des tCtracyclines sous laformede bases libres sont sensibles aux sites de protonation dans le cycle a A )). On observe un dCplacement de 14 ppm vers les hautes frCquences pour le forme cCtonique de I'oxytCtracycline (N protonee) par rapport a la forme Cnolique de 1'oxytCtracycline ( 0 protonCe). Une comparaison des dCplacements chirniques du 15N i I'etat solid6 et en solution indique pour la premikre fois que 1'intCgritC structurale (site de protonation ainsi que conformation) des tetracyclines est maintenue en solutions dans le (CD3)?SO. De plus, les spectres RMN du "N CP/MAS sont sensibles a des changements subtils de conformation du substituent amide du cycle x A n.

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“…Both compounds are broad-spectrum antibiotics and inhibit protein synthesis in bacteria by binding to the 30 S ribosomal subunit (10,11). Although the value of these compounds was readily apparent, it was several more years until the chemical structures were solved by the Woodward group (12,13). The tetracyclines are characterized by a unique C2 amide functionality and the linearly fused tetracyclic backbone, which is heavily decorated to yield the 2-naphthacene carboxamide aglycon (Fig.…”

Section: Oxytetracycline (Otc)mentioning

confidence: 99%

Oxytetracycline Biosynthesis

Pickens¹,

Tang

2010

Journal of Biological Chemistry

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Oxytetracycline (OTC) is a broad-spectrum antibiotic that acts by inhibiting protein synthesis in bacteria. It is an important member of the bacterial aromatic polyketide family, which is a structurally diverse class of natural products. OTC is synthesized by a type II polyketide synthase that generates the poly-␤-ketone backbone through successive decarboxylative condensation of malonyl-CoA extender units, followed by modifications by cyclases, oxygenases, transferases, and additional tailoring enzymes. Genetic and biochemical studies have illuminated most of the steps involved in the biosynthesis of OTC, which is detailed here as a representative case study in type II polyketide biosynthesis.

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The Structure of Terramycin^1,2

Cited by 164 publications

References 0 publications

Development and validation of an improved liquid chromatographic method for the analysis of oxytetracycline

Development and validation of an improved liquid chromatographic method for the analysis of oxytetracycline

A nitrogen-15 nuclear magnetic resonance study of the tetracycline antibiotics

Oxytetracycline Biosynthesis

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The Structure of Terramycin1,2

Cited by 164 publications

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Development and validation of an improved liquid chromatographic method for the analysis of oxytetracycline

Development and validation of an improved liquid chromatographic method for the analysis of oxytetracycline

A nitrogen-15 nuclear magnetic resonance study of the tetracycline antibiotics

Oxytetracycline Biosynthesis

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Product

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The Structure of Terramycin^1,2