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. 1969 Dec;115(4):797–805. doi: 10.1042/bj1150797

The configuration of 2,6-diamino-3-hydroxypimelic acid in microbial cell walls

H R Perkins 1
PMCID: PMC1185208  PMID: 4311441

Abstract

β-Hydroxydiaminopimelic acid, together with some diaminopimelic acid, occurs in the cell-wall mucopeptide of certain Actinomycetales. These components were converted into their di-DNP derivatives and separated by chromatography. Hence the relative proportions present in the cell walls of a number of species were measured. The problem of acid-induced inversion of configuration was studied. Of the diaminohydroxypimelic acids isomer B (see Scheme 2; amino groups meso, hydroxy group threo to its neighbouring amino group) always predominated but a small proportion of isomer D (amino groups l, hydroxy group erythro) also occurred. The configuration of the diaminohydroxypimelic acids was determined by periodate oxidation to glutamic γ-semialdehyde, which underwent spontaneous ring-closure. Reduction with sodium borohydride produced optically active proline, the configuration of which was determined by direct measurement of the optical rotation of DNP-proline. Un-cross-linked diaminohydroxypimelic acid in the cell wall was oxidized with periodate in the presence of ammonia. Since the remaining amino group was bound in peptide linkage, ring-closure was prevented and borohydride reduction of the aldehyde–ammonia presumed to be present resulted in the formation of ornithine. The quantity of ornithine was used as a measure of the degree of cross-linking.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BECKER B., LECHEVALIER M. P., LECHEVALIER H. A. CHEMICAL COMPOSITION OF CELL-WALL PREPARATIONS FROM STRAINS OF VARIOUS FORM-GENERA OF AEROBIC ACTINOMYCETES. Appl Microbiol. 1965 Mar;13:236–243. doi: 10.1128/am.13.2.236-243.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bricas E., Ghuysen J. M., Dezélée P. The cell wall peptidoglycan of Bacillus megaterium KM. I. Studies on the stereochemistry of alpha, alpha'-diaminopimelic acid. Biochemistry. 1967 Aug;6(8):2598–2607. doi: 10.1021/bi00860a043. [DOI] [PubMed] [Google Scholar]
  3. Ghuysen J. M. Use of bacteriolytic enzymes in determination of wall structure and their role in cell metabolism. Bacteriol Rev. 1968 Dec;32(4 Pt 2):425–464. [PMC free article] [PubMed] [Google Scholar]
  4. HAMILTON P. B., ANDERSON R. A. Hydroxylysine: isolation from gelatin and resolution of its diastereoisomers by ion exchange chromatography. J Biol Chem. 1955 Mar;213(1):249–258. [PubMed] [Google Scholar]
  5. HOARE D. S., WORK E. The stereoisomers of alpha epsilon-diaminopimelic acid. II. Their distribution in the bacterial order Actinomycetales and in certain Eubacteriales. Biochem J. 1957 Mar;65(3):441–447. doi: 10.1042/bj0650441. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. LEVY A. L. A paper chromatographic method for the quantitative estimation of amino-acids. Nature. 1954 Jul 17;174(4420):126–127. doi: 10.1038/174126a0. [DOI] [PubMed] [Google Scholar]
  7. Paz M. A., Lent R. W., Faris B., Franzblau C., Blumenfeld O. O., Gallop P. M. Aldehydes in native and denatured calf skin tropocollagen. Biochem Biophys Res Commun. 1969 Jan 27;34(2):221–229. doi: 10.1016/0006-291x(69)90635-4. [DOI] [PubMed] [Google Scholar]
  8. Perkins H. R. 2,6-Diamino-3-hydroxypimelic acid in microbial cell wall mucopeptide. Nature. 1965 Nov 27;208(5013):872–873. doi: 10.1038/208872a0. [DOI] [PubMed] [Google Scholar]
  9. Schleifer K. H., Plapp R., Kandler O. Die Aminosäuresequenz des Mureins von Microbacterium lacticum. Biochim Biophys Acta. 1968 Apr 9;154(3):573–582. [PubMed] [Google Scholar]
  10. Sundharadas G., Gilvarg C. A new synthesis and some biological properties of beta-hydroxy-alpha, epsilon-diaminopimelic acid. J Biol Chem. 1966 Jul 25;241(14):3276–3282. [PubMed] [Google Scholar]
  11. Szaniszlo P. J., Gooder H. Cell wall composition in relation to the taxonomy of some Actinoplanaceae. J Bacteriol. 1967 Dec;94(6):2037–2047. doi: 10.1128/jb.94.6.2037-2047.1967. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. WORK E. Reaction of ninhydrin in acid solution with straight-chain amino acids containing two amino groups and its application to the estimation of alpha epsilon-diaminopimelic acid. Biochem J. 1957 Nov;67(3):416–423. doi: 10.1042/bj0670416. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. YAMAGUCHI T. COMPARISON OF THE CELL-WALL COMPOSITION OF MORPHOLOGICALLY DISTINCT ACTINOMYCETES. J Bacteriol. 1965 Feb;89:444–453. doi: 10.1128/jb.89.2.444-453.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]

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