3-azidopropyl O-(3,8-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 1332835-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl O-(3,8-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: Kdn8Deoxya2-3LacbProN3
• CAS: 1332835-36-5
• 化学式: C₂₄H₄₁N₃O₁₈
• 分子量: 659.599
• InChiKey: JRSPZBZWIGRUQJ-JJKHPCOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.61
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  343.74
• 氢给体数：
  11.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  5-deoxyl-D-mannofuranoside 、 3-azidopropyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 N_. meningitidis CMP-sialic acid synthetase 、 Pasteurella multocida α2-3-sialyltransferase 、 Pasteurella multocida sialic acid aldolase 、 胞苷-5’-三磷酸 、 magnesium chloride 作用下， 以91%的产率得到3-azidopropyl O-(3,8-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  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