DOI: 10.1002/jms.1190300509. Recognition of cell‐wall peptide ligands by vancomycin group antibiotics: Studies using ion spray mass spectrometry

Recognition of cell‐wall peptide ligands by vancomycin group antibiotics: Studies using ion spray mass spectrometry

10.1002/jms.1190300509

Crossref journal-article

Wiley

Journal of Mass Spectrometry (311)

Abstract

AbstractNon‐covalent binding of antibiotics to their target ligands represents a form of molecular recognition which is of considerable contemporary interest in bioorganic and bioanalytical chemistry. The vancomycin antibiotics, including vancomycin and ristocetin, are a family of complex glycopeptides which bind specifically to the C‐terminal sequence X‐D‐Ala‐D‐Ala, where × is L‐lysine, L‐diaminopimelic acid, L‐alanine or L‐homoserine. It is shown that non‐covalent complexation of vancomycin and ristocetin with peptide ligands in solution, a key molecular recognition phenomenon in antibacterial chemotherapy, can be detected and analyzed in the gas phase by ionspray mass spectrometry. Using Nα,Nϵ‐diacetyl‐L‐Lys‐D‐Ala‐D‐Ala (Ac2KAA) as a representative ligand, it is further demonstrated that correlations of relative ion abundance with ligand concentrations in solution afford a direct method for measuring the binding constants of vancomycin and ristocetin complexes with target peptide sequences in bacterial cell wall. Results for ristocetin‐Ac2KAA (Ka = 6.25 × 105 l mol−1) and vancomycin‐Ac2KAA (Ka = 7.33 × 105 l mol−1, are in reasonable agreement with previously values [Ka = 5.9 × 105] and 1.5 × 106 l mol−1, respectively).

Bibliography

Lim, H., Hsieh, Y. L., Ganem, B., & Henion, J. (1995). Recognition of cellâwall peptide ligands by vancomycin group antibiotics: Studies using ion spray mass spectrometry. Journal of Mass Spectrometry, 30(5), 708â714. Portico.

Authors 4

Heng‐Keang Lim (first)
Yin Liang Hsieh (additional)
Bruce Ganem (additional)
Jack Henion (additional)

References 37 Referenced 103

{'key': 'e_1_2_1_2_2', 'first-page': '144', 'volume-title': 'The Molecular Basis of Antibiotic Action', 'author': 'Gale E. F.', 'year': '1981'} / The Molecular Basis of Antibiotic Action by Gale E. F. (1981)
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Dates

Type	When
Created	20 years, 3 months ago (May 31, 2005, 7:49 a.m.)
Deposited	1 year, 10 months ago (Oct. 27, 2023, 12:18 a.m.)
Indexed	2 months ago (June 30, 2025, 5:24 a.m.)
Issued	30 years, 4 months ago (May 1, 1995)
Published	30 years, 4 months ago (May 1, 1995)
Published Online	20 years, 4 months ago (April 14, 2005)
Published Print	30 years, 4 months ago (May 1, 1995)

Funders 0

None

BibTeX

@article{Lim_1995, title={Recognition of cell‐wall peptide ligands by vancomycin group antibiotics: Studies using ion spray mass spectrometry}, volume={30}, ISSN={1096-9888}, url={http://dx.doi.org/10.1002/jms.1190300509}, DOI={10.1002/jms.1190300509}, number={5}, journal={Journal of Mass Spectrometry}, publisher={Wiley}, author={Lim, Heng‐Keang and Hsieh, Yin Liang and Ganem, Bruce and Henion, Jack}, year={1995}, month=may, pages={708–714} }

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