(4E)-1S-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol | 1172607-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E)-1S-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol
• 英文别名: N-acetyl-α-D-galactopyranosyl 1-thio-7-oxaceramide；N-[(E,2R,3R)-1-[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl-3-hydroxy-6-undecoxyhex-4-en-2-yl]octadecanamide
• CAS: 1172607-59-8
• 化学式: C₄₃H₈₂N₂O₈S
• 分子量: 787.199
• InChiKey: OWQVQLOUFZQGHH-KIVMFWSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  54
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (4E)-1S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以96%的产率得到(4E)-1S-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol
  参考文献：
  名称：

  合成和评价ñ -乙酰基-2-氨基-2-脱氧α -D-半乳糖基-1-硫代-7- oxaceramide，一种新的模拟α -D-半乳糖基神经酰胺

  摘要：

  Abstractmagnified imageThe N‐acetyl‐2‐amino‐2‐deoxy‐α‐D‐galactopyranosyl 1‐thio‐7‐oxaceramide 1 was synthesized by substituting the 7‐oxasphingosine triflate 3 with α‐D‐N‐acetyl‐1‐thiogalactosamine (2). The triflate 3 was obtained from azide 4. Thiol 2 was prepared according to a known procedure from α‐D‐galactosamine hydrochloride. As compared to ceramide (Cer), 1 is neither a substrate of ceramide kinase (CerK), consistent with the absence of the C(1)OH group, nor an inhibitor of Cer phosphorylation by CerK. While 1 partially displaced CD1d‐bound lipids, it failed to stimulate invariant natural killer T (iNKT) cells when presented by human CD1d‐transfected cells. These results suggest that 1 binds weakly to recombinant CD1d, but does not form immunogenic complexes with CD1d.

  DOI：

  10.1002/hlca.200800454

文献信息

• Synthesis and Evaluation of<i>N</i>-Acetyl-2-amino-2-deoxy-<i>α</i>-D-galactosyl 1-Thio-7-oxaceramide, a New Analogue of<i>α</i>-D-Galactosyl Ceramide
  作者：Roshini Rajan、Thresen Mathew、Radovan Buffa、Frédéric Bornancin、Marco Cavallari、Peter Nussbaumer、Gennaro De Libero、Andrea Vasella

  DOI：10.1002/hlca.200800454

  日期：2009.5

  Abstractmagnified imageThe N‐acetyl‐2‐amino‐2‐deoxy‐α‐D‐galactopyranosyl 1‐thio‐7‐oxaceramide 1 was synthesized by substituting the 7‐oxasphingosine triflate 3 with α‐D‐N‐acetyl‐1‐thiogalactosamine (2). The triflate 3 was obtained from azide 4. Thiol 2 was prepared according to a known procedure from α‐D‐galactosamine hydrochloride. As compared to ceramide (Cer), 1 is neither a substrate of ceramide kinase (CerK), consistent with the absence of the C(1)OH group, nor an inhibitor of Cer phosphorylation by CerK. While 1 partially displaced CD1d‐bound lipids, it failed to stimulate invariant natural killer T (iNKT) cells when presented by human CD1d‐transfected cells. These results suggest that 1 binds weakly to recombinant CD1d, but does not form immunogenic complexes with CD1d.