Amino Acids

, Volume 21, Issue 3, pp 221–235

Determination of diamino acids in peptidoglycans from anaerobic bacteria

  • S. Satyanarayana
  • J. S. Grossert
  • S. F. Lee
  • R. L. White

DOI: 10.1007/s007260170008

Cite this article as:
Satyanarayana, S., Grossert, J., Lee, S. et al. Amino Acids (2001) 21: 221. doi:10.1007/s007260170008

Summary.

Peptidoglycans isolated from two Fusobacterium species of anaerobic bacteria were analyzed for constituent amino acids. Hydrolysis conditions were varied to optimize the yield of diamino acids from peptidoglycan. The o-phthalaldehyde derivatives of the diamino acid stereoisomers were separated by high-performance liquid chromatography (OPA-HPLC), and variations in the relative areas of the two peaks noticed during analysis of solid samples were attributed to sampling errors. Co-derivatization/injection experiments using standards of the meso and rac forms separated from commercial mixtures demonstrated that meso-2,6-diaminopimelic acid and meso-lanthionine were peptidoglycan components in Fusobacterium varium and Fusobacterium nucleatum, respectively. The protonated molecules of 2,6-diaminopimelic acid and lanthionine were detected in peptidoglycan hydrolyzates by off-line, flow-injection electrospray mass spectrometry (ESI-MS). In ESI-MS-MS experiments under identical collision-induced dissociation (CID) conditions, peptidoglycan-derived and standard diamino acids exhibited similar fragmentations. Fragmentation pathways are proposed for each diamino acid. The results confirm that the meso forms of two different diamino acids are utilized in the peptidoglycans of Fusobacterium species.

Keywords: Amino acids 6-Diaminopimelic acid Fusobacterium nucleatum Fusobacterium varium HPLC Lanthionine Electrospray mass spectrometry Peptidoglycan 

Copyright information

© Springer-Verlag Wien 2001

Authors and Affiliations

  • S. Satyanarayana
    • 1
  • J. S. Grossert
    • 1
  • S. F. Lee
    • 2
  • R. L. White
    • 1
  1. 1.Department of Chemistry, Dalhousie University,CA
  2. 2.Department of Applied Oral Sciences, Dalhousie University, andCA
  3. 3.Department of Microbiology and Immunology, Dalhousie University, Halifax, Nova Scotia, CanadaCA

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