Validamycin

Last updated
Validamycin
Validamycin.svg
Names
IUPAC name
(1R,2R,3S,4S,6R)-2,3-Dihydroxy-6-(hydroxymethyl)-4-{[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl β-D-glucopyranoside
Systematic IUPAC name
(2R,3R,4S,5S,6R)-2-{[(1R,2R,3S,4S,6R)-2,3-Dihydroxy-6-(hydroxymethyl)-4-{[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
Validamycin A; Valimon; Validacin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.120.044 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 609-372-4
KEGG
PubChem CID
UNII
  • InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11+,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1
    Key: JARYYMUOCXVXNK-IMTORBKUSA-N
  • InChI=1/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11+,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1
    Key: JARYYMUOCXVXNK-IMTORBKUBD
  • OC/C3=C/[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]3O
Properties
C20H35NO13
Molar mass 497.494 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Validamycin is an antibiotic and fungicide produced by Streptomyces hygroscopicus . An inhibitor of trehalase, [1] validamycin is used for the control of sheath blight of rice and damping-off of cucumbers.

See also

References

  1. ↑ Li, H.; Su, H.; Kim, S. B.; Chang, Y. K.; Hong, S. K.; Seo, Y. G.; Kim, C. J. (2011). "Enhanced production of trehalose in Escherichia coli by homologous expression of otsBA in the presence of the trehalase inhibitor, validamycin A, at high osmolarity". Journal of Bioscience and Bioengineering . 113 (2): 224–32. doi:10.1016/j.jbiosc.2011.09.018. PMID   22036231.
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