2,3'-disialyllactose | 1228473-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3'-disialyllactose
• 英文别名: NeuAc(a2-3)Gal(b1-4)[NeuAc(a2-2)]a-Glc；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-5-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1228473-86-6
• 化学式: C₃₄H₅₆N₂O₂₇
• 分子量: 924.816
• InChiKey: QKHAYQWWOKGTQG-ZXLDDDRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.7
• 重原子数：
  63
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  481
• 氢给体数：
  18
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  胞苷-5'-单磷酸-N-乙酰神经氨酸 、 乳糖 在 α2,3-sialyltransferase from Photobacterium sp. JT-ISH-224 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2,3'-disialyllactose
  参考文献：
  名称：

  An α2,3-Sialyltransferase fromPhotobacteriumsp. JT-ISH-224 TransfersN-Acetylneuraminic Acid to Both the O-2 and O-3′ Hydroxyl Groups of Lactose

  摘要：

  We found that 2,3-sialyltransferase from Photobacterium sp. JT-ISH-224 produced a regio-mistaken sialyl-transferred by-product. Spectroscopic analysis of the purified by-product indicated that it contained two N-acetylneuraminic acids: one attached to the O-3' hydroxyl group of lactose, and the other attached to the O-2 hydroxyl group of lactose. The relative configuration between the C-1 and C-3 of the -glucopyranose residue is superimposable with that between C-4 and C-2 of galactopyranoside. Therefore, formation of this by-product, designated 2,3'-disialyllactose, was simply rationalized as a regio-mistaken reaction of bacterial 2,3-sialyltransferase. This finding indicates that this bacterial 2,3-sialyltransferase has a possibility to synthesize several unusual sialosides.

  DOI：

  10.1080/07328300903586422

文献信息

• An α2,3-Sialyltransferase from<i>Photobacterium</i>sp. JT-ISH-224 Transfers<i>N</i>-Acetylneuraminic Acid to Both the O-2 and O-3′ Hydroxyl Groups of Lactose
  作者：Toshiki Mine、Hitomi Kajiwara、Takefumi Murase、Yasuhiro Kajihara、Takeshi Yamamoto

  DOI：10.1080/07328300903586422

  日期：2010.3.22

  We found that 2,3-sialyltransferase from Photobacterium sp. JT-ISH-224 produced a regio-mistaken sialyl-transferred by-product. Spectroscopic analysis of the purified by-product indicated that it contained two N-acetylneuraminic acids: one attached to the O-3' hydroxyl group of lactose, and the other attached to the O-2 hydroxyl group of lactose. The relative configuration between the C-1 and C-3 of the -glucopyranose residue is superimposable with that between C-4 and C-2 of galactopyranoside. Therefore, formation of this by-product, designated 2,3'-disialyllactose, was simply rationalized as a regio-mistaken reaction of bacterial 2,3-sialyltransferase. This finding indicates that this bacterial 2,3-sialyltransferase has a possibility to synthesize several unusual sialosides.