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Chemical Compound Review

Validacin     (2R,3R,4S,5S,6R)-2- [(1S,2S,3R,4R,6S)-2,3...

Synonyms: Valimon, VALIDAMYCIN A, HSDB 6745, AC1L1YAN, LS-84073, ...
 
 
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Disease relevance of Valimon

 

High impact information on Valimon

  • The resulting validamycin A from each of these feeding experiments was isolated, purified and analyzed by liquid scintillation counting, (2)H- or (13)C NMR or selective ion monitoring mass spectrometry (SIM-MS) techniques [1].
  • Genetic localization and heterologous expression of validamycin biosynthetic gene cluster isolated from Streptomyces hygroscopicus var. limoneus KCCM 11405 (IFO 12704) [4].
  • Deletion of a 30-kb DNA fragment from this cluster in the chromosome resulted in loss of validamycin production, confirming a direct involvement of the gene cluster in the biosynthesis of this important plant protectant [5].
  • Incorporation experiments with the labeled precursors in the validamycin A producer strain, Streptomyces hygroscopicus var. limoneus, revealed that the dehydration of 5-epi-valiolone to valienone occurs by a syn elimination of water [6].
  • Three of the overlapping cosmids (18G7, 5H3 and 9A2) also hybridized to the valA gene of the validamycin pathway from S. hygroscopicus 5008 as a probe [7].
 

Chemical compound and disease context of Valimon

  • The validamycin biosynthetic gene cluster was isolated from Streptomyces hygroscopicus var. limoneus KTCC 1715 (IFO 12704) using a pair of degenerated PCR primers designed from the sequence of AcbC, 2-epi-5-epi-valiolone synthase in the acarbose biosynthesis [4].
 

Biological context of Valimon

  • Validoxylamine A and validamycin A, two other trehalase inhibitors, showed potent competitive inhibition against purified pig kidney trehalase, with IC50 values of 2.4 x 10(-9) and 2.5 x 10(-4) M, respectively [8].
  • Alpha- or beta-Glucosidic linkage of validamycin was selectively cleaved by microbial hydrolysis and especially the conversion of validamycin C into validamycin A by the selective hydrolysis of alpha-glucoside linkage has important significance because validamycin C is considerably less active than validamycin A [9].
  • The biotransformation yield reached 92% when the reaction was performed at 37 degrees C for 1 h in the presence of 100 ml sodium phosphate buffer (0.1 M, pH 7.0), 32 mM validamycin A and 0.71 mg dry cell w/ml [3].
  • The purification and characterization of trehalase from common bean nodules as well as the role of this enzyme on growth, nodulation nitrogen fixation by examining the effects of the trehalase inhibitor validamycin A, was studied [10].
  • The studies reported here have established the biosynthetic origin of the mC7N units of acarbose and validamycin from sedo-heptulose 7-phosphate, and have identified 2-epi-5-epi-valiolone as the initial cyclization product [11].
 

Analytical, diagnostic and therapeutic context of Valimon

  • Relative standard deviation (RSD) values of MEKC determination of validamycin A in formulated products ranged from 0 [12].

References

  1. Biosynthesis of the validamycins: identification of intermediates in the biosynthesis of validamycin A by Streptomyces hygroscopicus var. limoneus. Dong, H., Mahmud, T., Tornus, I., Lee, S., Floss, H.G. J. Am. Chem. Soc. (2001) [Pubmed]
  2. Microbial degradation of validamycin A by Flavobacterium saccharophilum. Enzymatic cleavage of C-N linkage in validoxylamine A. Asano, N., Takeuchi, M., Ninomiya, K., Kameda, Y., Matsui, K. J. Antibiot. (1984) [Pubmed]
  3. Preparation of validoxylamine A by biotransformation of validamycin A using resting cells of a recombinant Escherichia coli. Yin, Y., Huang, W., Chen, D. Biotechnol. Lett. (2007) [Pubmed]
  4. Genetic localization and heterologous expression of validamycin biosynthetic gene cluster isolated from Streptomyces hygroscopicus var. limoneus KCCM 11405 (IFO 12704). Singh, D., Seo, M.J., Kwon, H.J., Rajkarnikar, A., Kim, K.R., Kim, S.O., Suh, J.W. Gene (2006) [Pubmed]
  5. Gene cluster responsible for validamycin biosynthesis in Streptomyces hygroscopicus subsp. jinggangensis 5008. Yu, Y., Bai, L., Minagawa, K., Jian, X., Li, L., Li, J., Chen, S., Cao, E., Mahmud, T., Floss, H.G., Zhou, X., Deng, Z. Appl. Environ. Microbiol. (2005) [Pubmed]
  6. Synthesis of 5-epi-[6-(2)H(2)]valiolone and stereospecifically monodeuterated 5-epi-valiolones: exploring the steric course of 5-epi-valiolone dehydratase in validamycin A biosynthesis. Mahmud, T., Xu, J., Choi, Y.U. J. Org. Chem. (2001) [Pubmed]
  7. Identification of genes necessary for jinggangmycin biosynthesis from Streptomyces hygroscopicus 10-22. Jian, X., Pang, X., Yu, Y., Zhou, X., Deng, Z. Antonie Van Leeuwenhoek (2006) [Pubmed]
  8. Inhibitors of pig kidney trehalase. Kyosseva, S.V., Kyossev, Z.N., Elbein, A.D. Arch. Biochem. Biophys. (1995) [Pubmed]
  9. Microbial transformation of validamycins. Kameda, Y., Horii, S., Yamano, T. J. Antibiot. (1975) [Pubmed]
  10. Physiological implications of trehalase from Phaseolus vulgaris root nodules: partial purification and characterization. García, N.A., Iribarne, C., López, M., Herrera-Cervera, J.A., Lluch, C. Plant Physiol. Biochem. (2005) [Pubmed]
  11. The biosynthesis of acarbose and validamycin. Mahmud, T., Lee, S., Floss, H.G. Chemical record (New York, N.Y.) (2001) [Pubmed]
  12. Determination of the antibiotic fungicide validamycin A in formulated products by micellar electrokinetic chromatography. Hsiao, Y.M., Lo, C.C. J. Agric. Food Chem. (1999) [Pubmed]
 
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