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Chemical Compound Review

sorbose     1,3,4,5,6-pentahydroxyhexan- 2-one

Synonyms: D-Psicose, L-sorbose, D-Tagatose, DL-Sorbose, DL-Tagatose, ...
 
 
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Disease relevance of fructose

 

Psychiatry related information on fructose

  • Feeding behavior in growing rats fed diets containing sorbose [6].
  • Furthermore, at 3 and 6 h, the post-thaw motility of the T group (36.3 +/- 2.4 and 25.0 +/- 2.0%, respectively) was significantly (P<0.05) higher than in the BSA (26.3 +/- 2.4 and 18.8 +/- 1.3%, respectively) and F (28.8 +/- 3.8 and 18.8 +/- 2.4%, respectively) groups [7].
 

High impact information on fructose

  • Loss and gain of chromosome 5 controls growth of Candida albicans on sorbose due to dispersed redundant negative regulators [8].
  • The specific activity of the transport system in vesicles, as determined by initial rate measurements of sorbose uptake, averaged 58% of that in erythrocytes [9].
  • The genes form an operon (gene order sorCpCDFBAE) and are inducible by L-sorbose [1].
  • Three mutants which were shown previously to have wide spectra of sensitivities to mutagens, and which exhibited reduced release of DNase activity on sorbose-containing agar test plates (the Nuh phenotype), were deficient relative to the wild-type in the release of these major alkaline DNases into the liquid culture medium [10].
  • The enzyme II complex can belong to one of six families based upon sequence similarity, with the sorbose transporter from Klebsiella pneumoniae a member of the mannose family.The structure of the IIB(Sor) domain was solved to 1.75A resolution by molecular replacement [11].
 

Chemical compound and disease context of fructose

 

Biological context of fructose

  • Most important, the multiple redundant regulators scattered along chromosome 5 explain, in a simple, elegant way, why the loss of the entire homologue is usually required for growth on sorbose [8].
  • For each O8:KX105 strain, a single plasmid ranging in size from 61 to 77 megadaltons carried the LT and STb genes.All of the enterotoxigenic O8: KX105 strains fermented sorbose, whereas the nonenterotoxigenic strain did not [16].
  • L-Sorbose metabolism in Klebsiella pneumoniae and Sor+ derivatives of Escherichia coli K-12 and chemotaxis toward sorbose [4].
  • The key steps of the process are the addition of organometallic reagents onto an L-sorbose-derived imine (13) followed by an internal reductive amination [17].
  • Genetics of L-sorbose transport and metabolism in Lactobacillus casei [14].
 

Anatomical context of fructose

  • However, in the absence of L-sorbose, the thermal stability of immobilized cells was lower [18].
  • Absolute and relative weights of abdominal fat were also decreased by increasing dietary sorbose [19].
  • It is possible that L-sorbose has some antiechinocytic properties and/or that it induces an alteration of red cell membrane flexibility [20].
  • A six test biotyping system comprising fermentation of dulcitol, sorbose, raffinose, and 5 ketogluconate, motility and production of beta-haemolysis was used to obtain biotype profiles for 514 strains of Escherichia coli isolated from the urinary tract [21].
  • 5. It is suggested that dietary sorbose, as a sweetener as well as a bulky agent, seems to be a suitable sugar for the obese and diabetic with special reference to lower body fat and energy deposition without reducing protein utilization [22].
 

Associations of fructose with other chemical compounds

  • METHODS: Prevention study: Male Sprague-Dawley rats were procured at 6 weeks of age and were divided into: control (C, n = 6), control-treated (CT, n = 5), fructose (F, n = 7) and fructose-treated (FT, n = 6) [3].
  • C. albicans biotyping determined the tolerance of the isolates to pH (pH 1.4) and salt; flucytosine, borate, and safranine resistance; and ability to produce proteinase and assimilate urea, sorbose, and citrate; results are expressed as three-digit numbers [23].
  • The alternative D-galactose degrading pathway of Aspergillus nidulans proceeds via L-sorbose [24].
  • For both proteins, a molecular mass of ca. 80 kDa was determined corresponding to a dimeric structure, an optimum pH at 7.5 and a temperature optimum at 35 degrees C. The enzyme oxidizes polyols like xylitol and D-sorbitol whereas the reduction reaction is preferred when providing D-xylulose, D-ribulose and L-sorbose as substrates [25].
  • The insertions also allowed determination of the direction of transcription of the gut gene, the newly mapped scr gene and of the sor gene cluster encoding enzymes for the metabolism of D-glucitol, sucrose and L-sorbose [26].
 

Gene context of fructose

 

Analytical, diagnostic and therapeutic context of fructose

References

  1. Cloning and physical mapping of the sor genes for L-sorbose transport and metabolism from Klebsiella pneumoniae. Wöhrl, B.M., Lengeler, J.W. Mol. Microbiol. (1990) [Pubmed]
  2. Purification and characterization of 5-ketofructose reductase from Erwinia citreus. Schrimsher, J.L., Wingfield, P.T., Bernard, A., Mattaliano, R., Payton, M.A. Biochem. J. (1988) [Pubmed]
  3. Chronic T-type Ca2+ channel blockade with mibefradil in hyperinsulinemic, insulin-resistant and hypertensive rats. Verma, S., Bhanot, S., Hicke, A., McNeill, J.H. Cardiovasc. Res. (1997) [Pubmed]
  4. L-Sorbose metabolism in Klebsiella pneumoniae and Sor+ derivatives of Escherichia coli K-12 and chemotaxis toward sorbose. Sprenger, G.A., Lengeler, J.W. J. Bacteriol. (1984) [Pubmed]
  5. Cloning and nucleotide sequencing of the membrane-bound L-sorbosone dehydrogenase gene of Acetobacter liquefaciens IFO 12258 and its expression in Gluconobacter oxydans. Shinjoh, M., Tomiyama, N., Asakura, A., Hoshino, T. Appl. Environ. Microbiol. (1995) [Pubmed]
  6. Feeding behavior in growing rats fed diets containing sorbose. Furuse, M., Tamura, Y., Matsuda, S., Shimizu, T., Okumura, J. Physiol. Behav. (1991) [Pubmed]
  7. Effects of bovine serum albumin and trehalose in semen diluents for improvement of frozen-thawed ram spermatozoa. Matsuoka, T., Imai, H., Kohno, H., Fukui, Y. J. Reprod. Dev. (2006) [Pubmed]
  8. Loss and gain of chromosome 5 controls growth of Candida albicans on sorbose due to dispersed redundant negative regulators. Kabir, M.A., Ahmad, A., Greenberg, J.R., Wang, Y.K., Rustchenko, E. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  9. Monosaccharide transport in protein-depleted vesicles from erythrocyte membranes. Zoccoli, M.A., Lienhard, G.E. J. Biol. Chem. (1977) [Pubmed]
  10. Alkaline deoxyribonucleases released from Neurospora crassa mycelia: two activities not released by mutants with multiple sensitivities to mutagens. Fraser, M.J. Nucleic Acids Res. (1979) [Pubmed]
  11. Crystal structure of the IIB(Sor) domain of the sorbose permease from Klebsiella pneumoniae solved to 1.75A resolution. Orriss, G.L., Erni, B., Schirmer, T. J. Mol. Biol. (2003) [Pubmed]
  12. Cloning of genes coding for L-sorbose and L-sorbosone dehydrogenases from Gluconobacter oxydans and microbial production of 2-keto-L-gulonate, a precursor of L-ascorbic acid, in a recombinant G. oxydans strain. Saito, Y., Ishii, Y., Hayashi, H., Imao, Y., Akashi, T., Yoshikawa, K., Noguchi, Y., Soeda, S., Yoshida, M., Niwa, M., Hosoda, J., Shimomura, K. Appl. Environ. Microbiol. (1997) [Pubmed]
  13. Prevention of the incidence of diabetes by dietary sorbose in nonobese diabetic mice. Furuse, M., Kimura, C., Takahashi, H., Okumura, J. J. Nutr. (1991) [Pubmed]
  14. Genetics of L-sorbose transport and metabolism in Lactobacillus casei. Yebra, M.J., Veyrat, A., Santos, M.A., Pérez-Martínez, G. J. Bacteriol. (2000) [Pubmed]
  15. L-Sorbose metabolism in Agrobacterium tumefaciens. Van Keer, C., Kersters, K., De Ley, J. Antonie Van Leeuwenhoek (1976) [Pubmed]
  16. Phenotypic and genotypic characterization of enterotoxigenic Escherichia coli serotype O8:KX105 and O8:K"2829" strains isolated from piglets with diarrhea. Broes, A., Fairbrother, J.M., Mainil, J., Harel, J., Lariviere, S. J. Clin. Microbiol. (1988) [Pubmed]
  17. A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate. Godin, G., Compain, P., Masson, G., Martin, O.R. J. Org. Chem. (2002) [Pubmed]
  18. Conversion of L-sorbose to L-sorbosone by immobilized cells of Gluconobacter melanogenus IFO 3293. Martin, C.K., Perlman, D. Biotechnol. Bioeng. (1976) [Pubmed]
  19. Regulation of lipid metabolism by dietary sorbose in laying hens. Furuse, M., Nakajima, S., Nakagawa, J., Shimizu, T., Okumura, J. Poult. Sci. (1990) [Pubmed]
  20. The influence of L-sorbose on red cell flow properties, shape and packing ability. Stäubli, M., Wälchli, P., Straub, P.W. Biorheology. (1985) [Pubmed]
  21. A concise biotyping system for differentiating strains of Escherichia coli. Gargan, R., Brumfitt, W., Hamilton-Miller, J.M. J. Clin. Pathol. (1982) [Pubmed]
  22. Lower fat deposition and energy utilization of growing rats fed diets containing sorbose. Furuse, M., Tamura, Y., Matsuda, S., Shimizu, T., Okumura, J. Comparative biochemistry and physiology. A, Comparative physiology. (1989) [Pubmed]
  23. Characterization of Candida isolates from pediatric burn patients. Neely, A.N., Odds, F.C., Basatia, B.K., Holder, I.A. J. Clin. Microbiol. (1988) [Pubmed]
  24. The alternative D-galactose degrading pathway of Aspergillus nidulans proceeds via L-sorbose. Fekete, E., Karaffa, L., Sándor, E., Bányai, I., Seiboth, B., Gyémánt, G., Sepsi, A., Szentirmai, A., Kubicek, C.P. Arch. Microbiol. (2004) [Pubmed]
  25. Characterization of the AXDH gene and the encoded xylitol dehydrogenase from the dimorphic yeast Arxula adeninivorans. Böer, E., Wartmann, T., Schmidt, S., Bode, R., Gellissen, G., Kunze, G. Antonie Van Leeuwenhoek (2005) [Pubmed]
  26. The use of lambda plac-Mu hybrid phages in Klebsiella pneumoniae and the isolation of stable Hfr strains. Wehmeier, U., Sprenger, G.A., Lengeler, J.W. Mol. Gen. Genet. (1989) [Pubmed]
  27. Role of the 14-3-3 protein in carbon metabolism of the pathogenic yeast Candida albicans. Wang, Y.K., Das, B., Huber, D.H., Wellington, M., Kabir, M.A., Sherman, F., Rustchenko, E. Yeast (2004) [Pubmed]
  28. Cloning of the Escherichia coli sor genes for L-sorbose transport and metabolism and physical mapping of the genes near metH and iclR. Wehmeier, U.F., Nobelmann, B., Lengeler, J.W. J. Bacteriol. (1992) [Pubmed]
  29. Dietary sorbose prevents and improves hyperglycemia in genetically diabetic mice. Furuse, M., Kimura, C., Mabayo, R.T., Takahashi, H., Okumura, J. J. Nutr. (1993) [Pubmed]
  30. NADPH-dependent L-sorbose reductase is responsible for L-sorbose assimilation in Gluconobacter suboxydans IFO 3291. Shinjoh, M., Tazoe, M., Hoshino, T. J. Bacteriol. (2002) [Pubmed]
  31. Genes for l-sorbose utilization in Escherichia coli. Woodward, M.J., Charles, H.P. J. Gen. Microbiol. (1982) [Pubmed]
  32. Cloning and restriction mapping of the L-sorbose utilization genes from a clinical isolate of Escherichia coli (1). Olukoya, D.K. African journal of medicine and medical sciences. (1993) [Pubmed]
 
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