3-deoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosonate | 1332835-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosonate
• 英文别名: Kdn8Me
• CAS: 1332835-33-2
• 化学式: C₁₀H₁₈O₉
• 分子量: 282.248
• InChiKey: LXIFPDJMEXGKQG-AVDKMFPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.36
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  156.91
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  benzyl 6-O-benzyl-2,3-O-isopropylidene-mannofuranoside 在 palladium 10% on activated carbon 、 Pasteurella multocida sialic acid aldolase 、 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.17h， 生成 3-deoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosonate
  参考文献：
  名称：

  Chemoenzymatic synthesis of C8-modified sialic acids and related α2–3- and α2–6-linked sialosides

  摘要：

  Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 ( PmNanA). In addition, alpha 2-3- and alpha 2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.083