5-acetamido-3,5-dideoxy-3-fluoro-D-erythro-L-gluco-2-nonulopyranosonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-3,5-dideoxy-3-fluoro-D-erythro-L-gluco-2-nonulopyranosonic acid
• 英文别名: D-ery-L-glcNon2ulo3F5NAc-onic；(3S,4R,5R,6R)-5-acetamido-3-fluoro-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₁₁H₁₈FNO₉
• 分子量: 327.264
• InChiKey: ALJLGESFXXDPKH-TYKOAFDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-acetamido-3,5-dideoxy-3-fluoro-D-erythro-L-gluco-2-nonulopyranosonic acid 、 甲基 4-O-BETA-D-半乳糖基-BETA-D-吡喃葡萄糖苷 在 Pasteurella multocida sialyltransferase Tris-HCl buffer 、 CMP-唾液酸合成酶 、 magnesium chloride 作用下， 以61%的产率得到methyl O-(5-acetamido-3,5-dideoxy-3-fluoro-D-erythro-β-L-gluco-2-nonulopyranosylonic acid)-(2-3)-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic Synthesis of Fluorinated Mechanistic Probes for Sialidases and Sialyltransferases

  摘要：

  A general, convenient, and efficient enzymatic approach for producing fluorinated mechanistic probes for sialidases and sialyltransferases is described. Other than the reported sialyltransferase inhibitor CMP-3F(axial)Neu5Ac, CIVIP-3F (equatorial)Sia derivatives (in which Sia is Neu5Ac or Neu5Gc) have been synthesized along with CMP-3F (axial)Neu5Gc and CMP-3F(axia/)KDN as novel inhibitors and important mechanistic probes for sialyltransferases. 3-Fluoro-sialosides have been enzymatically synthesized and could be used as potential inhibitors and mechanistic probes for sialidases and as probes for sialic acid-binding proteins.

  DOI：

  10.1021/ja072687u
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 、 β-氟丙酮酸钠盐 在 Tris-HCl buffer 、 magnesium chloride 作用下， 以52%的产率得到5-acetamido-3,5-dideoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonic acid
  参考文献：
  名称：

  Enzymatic Synthesis of Fluorinated Mechanistic Probes for Sialidases and Sialyltransferases

  摘要：

  A general, convenient, and efficient enzymatic approach for producing fluorinated mechanistic probes for sialidases and sialyltransferases is described. Other than the reported sialyltransferase inhibitor CMP-3F(axial)Neu5Ac, CIVIP-3F (equatorial)Sia derivatives (in which Sia is Neu5Ac or Neu5Gc) have been synthesized along with CMP-3F (axial)Neu5Gc and CMP-3F(axia/)KDN as novel inhibitors and important mechanistic probes for sialyltransferases. 3-Fluoro-sialosides have been enzymatically synthesized and could be used as potential inhibitors and mechanistic probes for sialidases and as probes for sialic acid-binding proteins.

  DOI：

  10.1021/ja072687u

文献信息

• Enzymatic Synthesis of Fluorinated Mechanistic Probes for Sialidases and Sialyltransferases
  作者：Harshal A. Chokhawala、Hongzhi Cao、Hai Yu、Xi Chen

  DOI：10.1021/ja072687u

  日期：2007.9.1

  A general, convenient, and efficient enzymatic approach for producing fluorinated mechanistic probes for sialidases and sialyltransferases is described. Other than the reported sialyltransferase inhibitor CMP-3F(axial)Neu5Ac, CIVIP-3F (equatorial)Sia derivatives (in which Sia is Neu5Ac or Neu5Gc) have been synthesized along with CMP-3F (axial)Neu5Gc and CMP-3F(axia/)KDN as novel inhibitors and important mechanistic probes for sialyltransferases. 3-Fluoro-sialosides have been enzymatically synthesized and could be used as potential inhibitors and mechanistic probes for sialidases and as probes for sialic acid-binding proteins.