4''-epi-validamycin A | 1039021-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4''-epi-validamycin A
• 英文别名: (2R,3R,4S,5R,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1039021-94-7
• 化学式: C₂₀H₃₅NO₁₃
• 分子量: 497.497
• InChiKey: JARYYMUOCXVXNK-SFKYOCBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  253
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4-(羟基甲基)-6-[[2,3,4-三羟基-5-(羟基甲基)环己基]氨基]环己-4-烯-1,2,3-三醇 、 uridine-5-diphosphate-α-D-galactose disodium salt 在 recombinant His₆-tagged validamycin glycosyltransferase 作用下， 以100%的产率得到4''-epi-validamycin A
  参考文献：
  名称：

  Catalytic Analysis of the Validamycin Glycosyltransferase (ValG) and Enzymatic Production of 4′′-epi-Validamycin A

  摘要：

  ValG is a glycosyltransferase (GT) that is responsible for the glucosylation of validoxylamine A to validamycin A. To explore the potential utilization of ValG as a tool for the production of validamycin analogues, a number of nucleotidyldiphosphate-sugars were evaluated as alternative substrates for ValG. The results indicated that in addition to its natural substrate, UDP-glucose, ValG also efficiently utilized UDP-galactose as sugar donor and resulted in the production of an unnatural compound, 4"-epi-validamycin A. The new compound demonstrated a moderate growth inhibitory activity against the plant fungal pathogen Rhizoctonia solani (=Pellicularia sasakii). A comparative analysis of ValG with its homologous proteins revealed that ValG contains an unusual DTG motif, in place of the DXD motif proposed for metal ion binding and/or NDP-sugar binding and commonly found in other glycosyltransferases. Site-directed mutagenesis of the DTG motif of ValG to DCD altered its preferences for metal ion binding, but did not seem to affect its substrate specificity.

  DOI：

  10.1021/np800185k