Structure of 6-O-methylerythromycin A (clarithromycin)

Iwasaki, Hitoshi; Sugawara, Yoichi; Adachi, Takashi; Morimoto, Shigeo; Watanabe, Yoshiaki

doi:10.1107/s0108270193000186

Cited by 31 publications

(19 citation statements)

References 4 publications

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“…5,6,7 The two sugar residues adopt a chair conformation. The desosamine ring is perpendicular to the macrolide ring and the cladinose ring is approximately parallel.…”

Section: Resultsmentioning

confidence: 99%

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD₂Cl₂ and D₂O from NMR constraints

Steinmetz

Sparrow

Somsouk

2004

Magnetic Reson in Chemistry

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The three-dimensional structure of the antibiotic oxolide, (9S,11S)-11-amino-9-deoxo-11,12-deoxy-9,12-epoxyerythromycin, was determined in CD2Cl2 through constrained molecular mechanics with constraints derived from proton NMR. The calculations yielded a well-defined global minimum. Data acquired for oxolide in D2O, although not as complete, indicate that the antibiotic adopts the same conformation in water.

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“…5,6,7 The two sugar residues adopt a chair conformation. The desosamine ring is perpendicular to the macrolide ring and the cladinose ring is approximately parallel.…”

Section: Resultsmentioning

confidence: 99%

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD₂Cl₂ and D₂O from NMR constraints

Steinmetz

Sparrow

Somsouk

2004

Magnetic Reson in Chemistry

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“…As noted by Ladam et al and co-workers 31 and Everett and Tyler, 32 these conformations can be arranged into two families: the folded-out conformation illustrated by the crystal structure of 6-O-methylerythromycin 25 and the folded-in conformation illustrated by the crystal structure of dirithromycin. 33 The differences between these two conformations are readily seen when one superimposes the heavy atoms in the macrolide backbone (see Fig.…”

Section: Conformation Of the Macrolide Ringmentioning

confidence: 94%

Determination of the aqueous‐phase structure of 6‐O‐methylerythromycin from NMR constraints

Steinmetz

Sadowsky

Rice

et al. 2001

Magnetic Reson in Chemistry

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The three-dimensional structure of the antibiotic 6-O-methylerythromycin in water was determined via constrained molecular mechanics using constraints derived from NMR spectra. The NMR structure is compared with its crystal structure and the structures of other derivatives of erythromycin. Distance constraints were obtained from NOESY, ROESY and GOESY spectra and torsional constraints from proton-proton and proton-carbon vicinal coupling constants. The modeling calculations employed Version 6.5 of SYBYL and the 1994 release of the Merck Molecular Force Field. The three-dimensional structure is defined by four structures that minimize the energy and satisfy all the experimental NMR data. It has the following characteristics: the macrolide ring adopts a folded-out conformation, the cladinose and desosamine rings adopt chair conformations, the cladinose ring is parallel to the plane of the macrolide ring and the desosamine ring is perpendicular to the macrolide ring.

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“…This solvate is, however, isostructural with the previously described methanol solvate of clarithromycin (6-O-methyl erythromycin) 11 and its nonsolvated pseudomorph, crystal form II. 3 The methanol solvate is a mono-solvate.…”

Section: Methanol Solvatementioning

confidence: 92%

Crystallographic Characterization of Several Erythromycin A Solvates: The Environment of The Solvent Molecules in the Crystal Lattice

Henry

Zhang

2007

Journal of Pharmaceutical Sciences

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Structure of 6-O-methylerythromycin A (clarithromycin)

Cited by 31 publications

References 4 publications

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD₂Cl₂ and D₂O from NMR constraints

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD₂Cl₂ and D₂O from NMR constraints

Determination of the aqueous‐phase structure of 6‐O‐methylerythromycin from NMR constraints

Crystallographic Characterization of Several Erythromycin A Solvates: The Environment of The Solvent Molecules in the Crystal Lattice

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Structure of 6-O-methylerythromycin A (clarithromycin)

Cited by 31 publications

References 4 publications

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD2Cl2 and D2O from NMR constraints

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD2Cl2 and D2O from NMR constraints

Determination of the aqueous‐phase structure of 6‐O‐methylerythromycin from NMR constraints

Crystallographic Characterization of Several Erythromycin A Solvates: The Environment of The Solvent Molecules in the Crystal Lattice

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Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD₂Cl₂ and D₂O from NMR constraints

Determination of the three‐dimensional, solution‐phase structure of the macrolide antibiotic oxolide in CD₂Cl₂ and D₂O from NMR constraints