(2-deoxy-2-(trimethylammonio)-α-D-glucopyranosyl)-(1,4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-2-acetamido-2-deoxy-D-glucitol | 1016264-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-deoxy-2-(trimethylammonio)-α-D-glucopyranosyl)-(1,4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-2-acetamido-2-deoxy-D-glucitol
• CAS: 1016264-89-3
• 化学式: C₃₃H₆₁N₄O₂₀
• 分子量: 833.862
• InChiKey: DVIBULAAXJAUKZ-OULVSQGPSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -8.97
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  365.21
• 氢给体数：
  14.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  (trimethylglucosaminium)chitotriomycin 在 sodium tetrahydroborate 作用下， 反应 2.0h， 以2.8 mg的产率得到(2-deoxy-2-(trimethylammonio)-α-D-glucopyranosyl)-(1,4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-2-acetamido-2-deoxy-D-glucitol
  参考文献：
  名称：

  TMG-chitotriomycin, an Enzyme Inhibitor Specific for Insect and Fungal β-N-Acetylglucosaminidases, Produced by Actinomycete Streptomyces anulatus NBRC 13369

  摘要：

  A novel beta-N-acetylglucosaminidase (GIcNAcase) inhibitor named TMG-chitotriomycin (1) was isolated from the culture filtrate of Streptomyces anulatus NBRC13369. The strain produced 1 only when colloidal chitin was used as the sole carbon source in the production medium. The structure of 1 was determined by spectral and constitutive sugar analyses of the corresponding alditol derivatives to be an equilibrated mixture of alpha-D-N,N,N-triMeGIcNH(2)-(1,4)-beta-D-GIcNAc-(1,4)-beta-D-GIcNAc-(1,4)-D-GlcNAc and its C-2 epimer of the reducing end residue. TMG-chitotriomycin (1) showed potent and selective inhibition of insect and fungal GIcNAcases with no inhibition of mammalian and plant GIcNAcases. In contrast, the known GIcNAcase inhibitor nagstatin potently inhibited all GIcNAcases. It should be emphasized that synthesized D-N,N,N-triMeGIcNH(2), which is the component sugar of 1, showed no inhibition of the insect Spodoptera litura GIcNAcase. These results suggest that the (GIcNAc)(3) unit positioned at the reducing end of 1 is essential for its enzyme inhibitory activity. The unique inhibitory spectrum of 1 will be useful to study chitinolytic systems and to develop selective fungicides or pesticides.

  DOI：

  10.1021/ja077641f