Skip to main content
PMC home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1972 Apr;110(1):110–116. doi: 10.1128/jb.110.1.110-116.1972

Identification of Products of the Uridinediphospho-N-acetyl-d-Glucosamine Oxidoreductase System from Citrobacter freundii ATCC 10053

Amiram Daniel 1,1, Rudolf A Raff 1,2, Robert W Wheat 1
PMCID: PMC247385  PMID: 4336107

Abstract

Uridinediphospho-N-acetyl glucosamine is converted to one or more uridine-diphospho-4-keto-6-deoxy-2-acetamidohexose derivatives by an enzyme from Citrobacter freundii ATCC 10053. Borohydride reduction of reaction products followed by acid hydrolysis yielded several amino sugars. Two of these were identified as fucosamine and quinovosamine by chromatography and ninhydrin degradation.

Full text

PDF
110

Selected References

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

  1. BARRY G. T., ROARK E. L-FUCOSAMINE AND 4-OXO-NORLEUCINE AS CONSTITUENTS IN MUCOPOLYSACCHARIDES OF CERTAIN ENTERIC BACTERIA. Nature. 1964 May 2;202:493–494. doi: 10.1038/202493a0. [DOI] [PubMed] [Google Scholar]
  2. BERNAERTS M. J., FURNELLE J., DE LEY J. The preparation of some new disaccharides and D-allose from 3-ketoglycosides. Biochim Biophys Acta. 1963 Feb 5;69:322–330. doi: 10.1016/0006-3002(63)91265-4. [DOI] [PubMed] [Google Scholar]
  3. BOAS N. F. Method for the determination of hexosamines in tissues. J Biol Chem. 1953 Oct;204(2):553–563. [PubMed] [Google Scholar]
  4. BOSE J. L., FOSTER A. B., STACEY M., WEBBER J. M. Action of manganese dioxide on simple carbohydrates. Nature. 1959 Oct 24;184:1301–1303. doi: 10.1038/1841301a0. [DOI] [PubMed] [Google Scholar]
  5. Brownlee S. T., Wheat R. W. On the determination of galactosamine-uronic acid. Anal Biochem. 1966 Mar;14(3):414–420. doi: 10.1016/0003-2697(66)90283-1. [DOI] [PubMed] [Google Scholar]
  6. CRUMPTON M. J., DAVIES D. A. The isolation of D-fucosamine from the specific polysaccharide of Chromobacterium violaceum (NCTC 7917). Biochem J. 1958 Dec;70(4):729–736. doi: 10.1042/bj0700729. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. DISCHE Z., SHETTLES L. B. A new spectrophotometric test for the detection of methylpentose. J Biol Chem. 1951 Oct;192(2):579–582. [PubMed] [Google Scholar]
  8. Distler J., Kaufman B., Roseman S. Enzymic synthesis of a diamino sugar nucleotide by extracts of type XIV Diplococcus pneumoniae. Arch Biochem Biophys. 1966 Sep 26;116(1):466–478. doi: 10.1016/0003-9861(66)90054-3. [DOI] [PubMed] [Google Scholar]
  9. GILBERT J. M., MATSUHASHI M., STROMINGER J. L. THYMIDINE DIPHOSPHATE 4-ACETAMIDO-4,6-DIDEOXYHEXOSES. II. PURIFICATION AND PROPERTIES OF THYMIDINE DIPHOSPHATE D-GLUCOSE OXIDOREDUCTASE. J Biol Chem. 1965 Mar;240:1305–1308. [PubMed] [Google Scholar]
  10. GINSBURG V. SUGAR NUCLEOTIDES AND THE SYNTHESIS OF CARBOHYDRATES. Adv Enzymol Relat Areas Mol Biol. 1964;26:35–88. doi: 10.1002/9780470122716.ch2. [DOI] [PubMed] [Google Scholar]
  11. LANNING M. C., COHEN S. S. The detection and estimation of 2-ketohexonic acids. J Biol Chem. 1951 Mar;189(1):109–114. [PubMed] [Google Scholar]
  12. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  13. MATSUHASHI M., STROMINGER J. L. THYMIDINE DIPHOSPHATE 4-ACETAMIDO-4, 6-DIDEOXYHEXOSES. I. ENZYMATIC SYNTHESIS BY STRAINS OF ESCHERICHIA COLI. J Biol Chem. 1964 Aug;239:2454–2463. [PubMed] [Google Scholar]
  14. Matsuhashi S., Matsuhashi M., Brown J. G., Strominger J. L. Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexoses. 3. Cytidine diphosphate D-glucose oxidoreductase. J Biol Chem. 1966 Sep 25;241(18):4283–4287. [PubMed] [Google Scholar]
  15. OKAZAKI R., OKAZAKIT, STROMINGER J. L., MICHELSON A. M. Thymidine diphosphate 4-keto-6-deoxy-d-glucose, an intermediate in thymidine diphosphate L-rhamnose synthesis in Escherichia coli strains. J Biol Chem. 1962 Oct;237:3014–3026. [PubMed] [Google Scholar]
  16. Oashi H., Matsuhashi M., Matsuhashi S. Thymidine diphosphate 4-acetamido-4,6-dideoxyhexoses. IV. Purification and properties of thymidine diphosphate 4-keto-6-deoxy-D-glucose transaminase from Pasteurella pseudotuberculosis. J Biol Chem. 1971 Apr 25;246(8):2325–2330. [PubMed] [Google Scholar]
  17. PARK J. T., JOHNSON M. J. A submicrodetermination of glucose. J Biol Chem. 1949 Nov;181(1):149–151. [PubMed] [Google Scholar]
  18. REISSIG J. L., STORMINGER J. L., LELOIR L. F. A modified colorimetric method for the estimation of N-acetylamino sugars. J Biol Chem. 1955 Dec;217(2):959–966. [PubMed] [Google Scholar]
  19. STOFFYN P. J., JEANLOZ R. W. Identification of amino sugars by paper chromatography. Arch Biochem Biophys. 1954 Oct;52(2):373–379. doi: 10.1016/0003-9861(54)90137-x. [DOI] [PubMed] [Google Scholar]
  20. Steele R. S., Brendel K., Scheer E., Wheat R. W. Ion-exchange separation and automated assay of complex mixtures of amino acids and hexosamines. Anal Biochem. 1970 Mar;34:206–225. doi: 10.1016/0003-2697(70)90101-6. [DOI] [PubMed] [Google Scholar]
  21. TREVELYAN W. E., PROCTER D. P., HARRISON J. S. Detection of sugars on paper chromatograms. Nature. 1950 Sep 9;166(4219):444–445. doi: 10.1038/166444b0. [DOI] [PubMed] [Google Scholar]
  22. VOLK W. A., ASHWELL G. Enzymatic formation of TDP-3-acetamido-3,6-dideoxy hexose. Biochem Biophys Res Commun. 1963 Jul 18;12:116–120. doi: 10.1016/0006-291x(63)90245-6. [DOI] [PubMed] [Google Scholar]
  23. WHEAT R. W., ROLLINS E. L., LEATHERWOOD J. M., BARNES R. L. Studies on the cell wall of Chromobacterium violaceum: the separation of lipopolysaccharide and mucopeptide by phenol extraction of whole cells. J Biol Chem. 1963 Jan;238:26–29. [PubMed] [Google Scholar]
  24. Wang S. F., Gabriel O. Biological mechanisms involved in the formation of deoxysugars. VI. Role and function of enzyme-bound nicotinamide adenine dinucleotide in thymidine diphosphate D-glucose oxidoreductase. J Biol Chem. 1970 Jan 10;245(1):8–14. [PubMed] [Google Scholar]
  25. Zarkowsky H., Lipkin E., Glaser L. The mechanism of 6-deoxyhexose synthesis IV. The role of pyridine nucleotide in substrate release. Biochem Biophys Res Commun. 1970 Feb 20;38(4):787–793. doi: 10.1016/0006-291x(70)90650-9. [DOI] [PubMed] [Google Scholar]
  26. Zarkowsky H., Lipkin E., Glaser L. The mechanism of 6-deoxyhexose synthesis. V. The relation of pyridine nucleotide to the structure of the deoxythymidine diphosphate-glucose oxidoreductase. J Biol Chem. 1970 Dec 25;245(24):6599–6606. [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES