3-(α-acarviosinyl-(1->6)-α-D-1-deoxyglucopyranos-1-yl)propene | 1039471-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(α-acarviosinyl-(1->6)-α-D-1-deoxyglucopyranos-1-yl)propene
• 英文别名: (2R,3S,4R,5R,6R)-2-[[(2S,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxymethyl]-6-prop-2-enyloxane-3,4,5-triol
• CAS: 1039471-07-2
• 化学式: C₂₂H₃₇NO₁₂
• 分子量: 507.535
• InChiKey: LGWXYCLTOWZHIZ-OISWNILPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  222
• 氢给体数：
  10
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5S,6R)-2-allyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 、 amylostatin XG 在 Thermus sp. maltogenic amylase 、 水 作用下， 反应 24.0h， 以10%的产率得到3-(α-acarviosinyl-(1->4)-α-D-1-deoxyglucopyranos-1-yl)propene
  参考文献：
  名称：

  Enzymatic Synthesis of a Selective Inhibitor for α-Glucosidases: α-Acarviosinyl-(1→9)-3-α-d-glucopyranosylpropen

  摘要：

  Here, we describe the enzymatic synthesis of novel inhibitors using acarviosine-glucose, as a donor and 3-alpha-D-glucopyranosylpropen (alpha GP) as an acceptor. Maltogenic amylase from Thermus sp. (ThMA) catalyzed the transglycosylation of the acarviosine moiety to alpha GP. The two major reaction products were isolated using chromatographies. Structural analyses revealed that acarviosine was transferred to either C-7 or C-9 of the alpha GP, which correspond to C-4 and C-6 of glucose. Both inhibited rat intestine (x-glucosidase competitively but displayed a mixed-type inhibition mode against human pancreatic alpha-amylase. The alpha-acarviosinyl-(1 -> 7)-3-alpha-D-glucopyranosylpropen showed weaker inhibition potency than acarbose against both alpha-glycosidases. In contrast, the alpha-acarviosinyl-(1 -> 9)-3-alpha-D-glucopyranosylpropen exhibited a 3.0-fold improved inhibition potency against rat intestine a-glucosidase with 0.3-fold inhibition potency against human pancreatic a-amylase relative to acarbose. In conclusion, alpha-acarviosinyl-(1 -> 9)-3-alpha-D-glucopyranosylpropen is a novel alpha-glucosidase-selective inhibitor with 10-fold enhanced selectivity toward alpha-glucosidase over alpha-amylase relative to acarbose, and it could be applied as a potent hypoglycemic agent.

  DOI：

  10.1021/jf703655k