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Chemical Compound Review

Quinovose     (2S,3R,4S,5S,6R)-6- methyloxane-2,3,4,5-tetrol

Synonyms: SureCN79180, CHEBI:42606, ZINC02042980, AC1L9B8Y, C08352, ...
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Disease relevance of alpha-D-Quinovopyranose


High impact information on alpha-D-Quinovopyranose

  • Km values for glucose, 6-deoxyglucose, and 3-O-methylglucose of 1.5 x 10(-5) M, 2.7 x 10(-4) M, and 1.0 x 10(-3) M, respectively, were identical in Chlorella and in S. pombe cells transformed with Chlorella cDNA and approximately 100-fold lower than those of the endogenous transport system of S. pombe [2].
  • When glucose or the nonmetabolizable analogue 6-deoxyglucose is added to the cells, an increased expression of GAPDH or AAT is observed after 10 or 30 min, respectively [3].
  • ORFs 3 and 4 (tylA1 and tylA2) encode delta TDP-glucose synthase and delta TDP-glucose dehydratase, respectively, enzymes responsible for the first two steps common to the biosynthesis of all three deoxyhexose sugars of tylosin via the common intermediate, delta TDP-4-keto, 6-deoxyglucose [4].
  • By testing other Glc analogs, we found that 2-deoxyglucose, which, like Man, is phosphorylated by HXK, also blocked germination; no inhibition was observed with 6-deoxyglucose or 3-O-methylglucose, which are not substrates for HXK [5].
  • CONCLUSIONS: beta-SQDG(18:0) might be a new class of the immunosuppressive reagent, and the inhibition of responder T-lymphocyte activation in MLR by beta-SQDG(18:0) may be responsible for certain three-dimensional structures of this reagent or its quinovose binding to sulfonic acid [6].

Biological context of alpha-D-Quinovopyranose


Anatomical context of alpha-D-Quinovopyranose

  • However, when the surface proteins of the spermatozoa were labelled with radioactive iodine, the sperm surface proteins alpha-chlorohydrin and 6CDG treated animals were found to differ from those of the control animals [9].

Associations of alpha-D-Quinovopyranose with other chemical compounds


Gene context of alpha-D-Quinovopyranose


  1. Protonmotive force driven 6-deoxyglucose uptake by the oral pathogen, Streptococcus mutans Ingbritt. Keevil, C.W., McDermid, A.S., Marsh, P.D., Ellwood, D.C. Arch. Microbiol. (1986) [Pubmed]
  2. Functional expression of the Chlorella hexose transporter in Schizosaccharomyces pombe. Sauer, N., Caspari, T., Klebl, F., Tanner, W. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  3. Glucose increases the expression of the ATP/ADP translocator and the glyceraldehyde-3-phosphate dehydrogenase genes in Chlorella. Hilgarth, C., Sauer, N., Tanner, W. J. Biol. Chem. (1991) [Pubmed]
  4. Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome. Merson-Davies, L.A., Cundliffe, E. Mol. Microbiol. (1994) [Pubmed]
  5. Mannose inhibits Arabidopsis germination via a hexokinase-mediated step. Pego, J.V., Weisbeek, P.J., Smeekens, S.C. Plant Physiol. (1999) [Pubmed]
  6. An immunosuppressive effect by synthetic sulfonolipids deduced from sulfonoquinovosyl diacylglycerols of sea urchin. Matsumoto, Y., Sahara, H., Fujita, T., Shimozawa, K., Takenouchi, M., Torigoe, T., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., Mizushina, Y., Ohta, K., Takahashi, N., Gasa, S., Jimbow, K., Sakaguchi, K., Sato, N. Transplantation (2002) [Pubmed]
  7. The determination of the membrane ptoential of Chlorella vulgaris. Evidence for electrogenic sugar transport. Komor, E., Tanner, W. Eur. J. Biochem. (1976) [Pubmed]
  8. Carbohydrate-specific antibodies in normal human sera. I. Characterization of specificity for beta-D-glucose. Lalezari, P., Jiang, A.F., Kumar, M., Lalezari, I. Vox Sang. (1984) [Pubmed]
  9. Effects of antifertility drugs on epididymal protein secretion, acquisition of sperm surface proteins and fertility in male rats. Tsang, A.Y., Lee, W.M., Wong, P.Y. Int. J. Androl. (1981) [Pubmed]
  10. Activation of adenylate cyclase in cdc25 mutants of Saccharomyces cerevisiae. Pardo, L.A., Lazo, P.S., Ramos, S. FEBS Lett. (1993) [Pubmed]
  11. Signals related to glucose metabolism regulate islet amyloid polypeptide (IAPP) gene expression in human pancreatic islets. Gasa, R., Gomis, R., Casamitjana, R., Novials, A. Regul. Pept. (1997) [Pubmed]
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