(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose | 64003-53-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose
• 英文别名: N-acetyl-alpha-neuraminosyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosamine-(1->3)-beta-D-galactose-(1->4)-D-glucose；(2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 64003-53-8
• 化学式: C₃₇H₆₁N₂O₂₉
• 分子量: 997.887
• InChiKey: IOAPDMZSLCJVCR-OYHBKBROSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -9.7
• 重原子数：
  68
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  505
• 氢给体数：
  18
• 氢受体数：
  29

安全信息

• WGK Germany：
  3
• 海关编码：
  29329990

反应信息

• 作为反应物：
  描述：

  (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose 、 cytidine monophospho-N-acetylneuraminic acid 生成 (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)<(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-6)>-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galact... 、 cytidine 5'-monophosphate 、 氢(+1)阳离子
  参考文献：
  名称：

  Biosynthesis of a disialylated sequence in N-linked oligosaccharides: identification of an N-acetylglucosaminide (alpha26)-sialyltransferase in Golgi apparatus from rat liver

  摘要：

  Rat liver Golgi apparatus are shown to have a CMP-N-acetylneuraminate: N-acetylglucosaminide (alpha 2----6)-sialyltransferase which catalyzes the conversion of the human milk oligosaccharide LS-tetrasaccharide-a (NeuAc alpha 2----3Gal beta 1---- 3GlcNAc beta 1----3Gal beta 1----4Glc) to disialyllacto -N- tetraose containing the terminal sequence: (formula: see text) found in N-linked oligosaccharides of glycoproteins. The N-acetylglucosaminide (alpha 2----6)-sialyltransferase has a marked preference for the sequence NeuAc alpha 2----3-Gal beta 1---- 3GlcNAc as an acceptor substrate. Thus, the order of addition of the two sialic acids in the disialylated structure shown above is proposed to be first the terminal sialic acid in the NeuAc alpha 2----3Gal linkage followed by the internal sialic acid in the NeuAc alpha 2---- 6GlcNAc linkage. Sialylation in vitro of the type 1 branches (Gal beta 1---- 3GlcNAc -) of the N-linked oligosaccharides of asialo prothrombin to produce the same disialylated sequence is also demonstrated.

  DOI：

  10.1111/j.1432-1033.1984.tb08133.x
• 作为产物：
  描述：

  lacto-N-tetraose 、 胞苷-5'-单磷酸-N-乙酰神经氨酸 在 Galβ1,3(4)GlcNAc α2,3 sialyltransferase 、 Triton-CF 54 、 sodium cacodylate 、 bovine serum albumin 作用下， 反应 48.0h， 生成 (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose
  参考文献：
  名称：

  Combined chemical and enzymatic synthesis of sialyloligosaccharides and characterization by 500-MHz and proton and carbon-13 NMR spectroscopy

  摘要：

  DOI：

  10.1021/ja00268a056