Complete assignment of the 13C NMR spectrum of vancomycin

Pearce, Clive M.; Williams, Dudley H.

doi:10.1039/p29950000153

Cited by 26 publications

(20 citation statements)

References 8 publications

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“…These observations suggest that C-O-D and D-O-E biaryl ethers have adopted the same atropisomer as found in vancomycin. [17][18][19]28 A large NOE is observed between protons X5 and X6 in both oritavancin and 4 and this is consistent with the presences of a cis-amide bond between amino acid residues 5 and 6, a conformation that is also common in a variety of vancomycin analogs. The observed NOE intensities between proton B2 and those at positions X5, X6, and W7 were strong in oritavancin and medium to weak in 4 (see Fig.…”

Section: Structural Elucidation Studies By Nmrsupporting

confidence: 70%

“…17 NMR studies of vancomycin in solution have shown that the backbone conformation of the cyclic peptide correlates well with structural data obtained from the X-ray diffraction studies. 20 However, from these studies, the first amino acid residue and the glucose-vancosamine rings were observed to have considerable conformational flexibility in solution.…”

Section: Structural Elucidation Studies By Nmrmentioning

confidence: 68%

“…12,13 The structural characterization of vancomycin required a significant effort due to the complexity of its multi-ringed system. While early work relied heavily on chemical degradation analysis, within recent years the structure of intact vancomycin has been extensively investigated by using NMR [17][18][19] spectroscopy and X-ray crystallography. 20 The results of these studies show that all of the amide bonds in vancomycin adopt the trans conformation, except for the amide between amino acids 5 and 6, and the AB-biaryl, D-O-E and C-O-D biaryl ethers are found in the S configuration (see Fig.…”

Section: Introductionmentioning

confidence: 99%

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Formation, isolation and characterization of an AB-biaryl atropisomer of oritavancin

et al. 2004

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Section: Structural Elucidation Studies By Nmrsupporting

confidence: 70%

Section: Structural Elucidation Studies By Nmrmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 99%

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Formation, isolation and characterization of an AB-biaryl atropisomer of oritavancin

et al. 2004

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“…Nuclear magnetic resonance (NMR) spectral data for vancomycin powder 31 showed that typical vancomycin peaks were recovered after isostatic compression.…”

Section: Characterization Of Vancomycinmentioning

confidence: 99%

Influence of isostatic compression on the stability of vancomycin loaded with a calcium phosphate-implantable drug delivery device

Gautier

Caillon²,

Ray

et al. 2000

J. Biomed. Mater. Res.

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It is essential to prevent microbial infections after osteoarticular trauma or prosthesis implantation. As an alternative to antibiotic parenteral administration, antibiotic-loaded biomaterials allow high concentrations to be obtained in situ without systemic toxicity. Although the formulation of biphasic calcium-phosphate (BCP)-vancomycin granules by isostatic compression has recently been used to produce drug-delivery devices, the stability of vancomycin needs to be proven. In this study, vancomycin was associated with BCP powders by isostatic compression at 100, 140, or 200 MPa and then extracted or released by a rotating paddle system for 24 h. Vancomycin assays were performed by spectrophotometric and microbiological methods. The results show that all vancomycin associated with the material was recovered after extraction without degradation. Thus, vancomycin was not denaturated after application of 100, 140, or 200 MPa of isostatic compression. The results for vancomycin released from granules compressed at the three pressures were not significantly different (p =.01) whether assays were performed microbiologically or spectrophotometrically, indicating a good correlation between the two methods. This process involving high pressure appears to be a good means of developing drug delivery devices loaded with therapeutic agents without denaturating the components.

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“…The molecular interactions of glycopeptide antibiotics with cell wall precursor analogs have been studied by a variety of analytical techniques such as UV difference spectroscopy [6], nuclear magnetic resonance (NMR) [19,20], surface plasmon resonance (SPR) [21], and X-ray crystallography [22]. In recent years, bioaffinity mass spectrometry (MS) [23][24][25] and affinity capillary electrophoresis (ACE) [23,26,27] have emerged as relatively new techniques to probe molecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Molecular interactions of glycopeptide antibiotics investigated by affinity capillary electrophoresis and bioaffinity electrospray ionization‐mass spectrometry

et al. 2002

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Many analytical approaches are available to evaluate (bio)molecular interactions, all of which have their particular advantages and disadvantages. In recent years, two relatively new techniques have emerged that may be used by the bioanalytical community to evaluate such interactions, namely affinity capillary electrophoresis (ACE) and bioaffinity electrospray ionization-mass spectrometry (ESI-MS). In this paper, we describe and evaluate the use of both these techniques for the investigation of the interactions of glycopeptide antibiotics with peptides that mimic the bacterial cell wall binding site. We focus particularly on the effect of the sugar moieties attached to the antibiotic peptide backbone and on the noncovalent dimerization of these glycopeptide antibiotics.

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Complete assignment of the 13C NMR spectrum of vancomycin

Cited by 26 publications

References 8 publications

Formation, isolation and characterization of an AB-biaryl atropisomer of oritavancin

Formation, isolation and characterization of an AB-biaryl atropisomer of oritavancin

Influence of isostatic compression on the stability of vancomycin loaded with a calcium phosphate-implantable drug delivery device

Molecular interactions of glycopeptide antibiotics investigated by affinity capillary electrophoresis and bioaffinity electrospray ionization‐mass spectrometry

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