lithium [(5-amino-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onate] (cytidin-5'-yl) phosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: lithium [(5-amino-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onate] (cytidin-5'-yl) phosphate
• 英文别名: lithium;[(2R,4S,5R,6R)-5-amino-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl] [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• 化学式: C₁₈H₂₈N₄O₁₅P*Li
• 分子量: 578.353
• InChiKey: HNCUGOYEHCNMTC-AFVCJCPKSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -9.08
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  320
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  diethyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-2-nonulopyranosyl)onate] phosphite 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 lithium [(5-amino-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onate] (cytidin-5'-yl) phosphate
  参考文献：
  名称：

  Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

  摘要：

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e