Neu5NAcα2->3lactose alditol | 65907-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Neu5NAcα2->3lactose alditol
• 英文别名: Neu5Ac(α2->3)lactitol；Neu5Acα2-3Galβ1-4Glc；NeuAc(a2-3)Gal(b1-?)Glc-ol；(2S,4S,5R,6R)-5-acetamido-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4R,5S)-1,2,4,5,6-pentahydroxyhexan-3-yl]oxyoxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 65907-88-2
• 化学式: C₂₃H₄₁NO₁₉
• 分子量: 635.574
• InChiKey: HTAGRCVASQXJKI-FHHHURIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.7
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  346
• 氢给体数：
  14
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  苯甲酸酐 、 Neu5NAcα2->3lactose alditol 在 N-甲基咪唑 作用下， 反应 5.0h， 生成
  参考文献：
  名称：

  Mass Spectrometric Analysis of Benzoylated Sialooligosaccharides and Differentiation of Terminal α2→3 and α2→6 Sialogalactosylated Linkages at Subpicomole Levels

  摘要：

  发现过苯甲酰化唾液酸低聚糖是稳定的衍生物，在正离子模式下的基质辅助激光解吸/电离 (MALDI) 质谱分析过程中发出强烈的信号。寡糖的末端 Neu5NAcα2→3 和 α2→6Gal 单元在苯甲酰化过程中会发生特征性结构变化，产生易于识别的质谱模式。亚皮摩尔碳水化合物样品成功苯甲酰化，并通过 MALDI 质谱进行分析。

  DOI：

  10.1021/ac990674w
• 作为产物：
  描述：

  3'-sialyllactose 在 sodium tetrahydroborate 作用下， 反应 3.0h， 生成 Neu5NAcα2->3lactose alditol
  参考文献：
  名称：

  Mass Spectrometric Analysis of Benzoylated Sialooligosaccharides and Differentiation of Terminal α2→3 and α2→6 Sialogalactosylated Linkages at Subpicomole Levels

  摘要：

  发现过苯甲酰化唾液酸低聚糖是稳定的衍生物，在正离子模式下的基质辅助激光解吸/电离 (MALDI) 质谱分析过程中发出强烈的信号。寡糖的末端 Neu5NAcα2→3 和 α2→6Gal 单元在苯甲酰化过程中会发生特征性结构变化，产生易于识别的质谱模式。亚皮摩尔碳水化合物样品成功苯甲酰化，并通过 MALDI 质谱进行分析。

  DOI：

  10.1021/ac990674w

文献信息

• The trans-sialidase from Trypanosoma cruzi efficiently transfers α-(2→3)-linked N-glycolylneuraminic acid to terminal β-galactosyl units
  作者：Rosalía Agustí、María Eugenia Giorgi、Rosa M. de Lederkremer

  DOI：10.1016/j.carres.2007.07.018

  日期：2007.11

  The trans-sialidase from Trypanosoma cruzi (TcTS), the agent of Chagas' disease, is a unique enzyme involved in mammalian host-cell invasion. Since T cruzi is unable to synthesize sialic acids de novo, TcTS catalyzes the transfer of alpha-(2 -> 3)-sialyl residues from the glycoconjugates of the host to terminal beta-galactopyranosyl units present on the surface of the parasite. TcTS also plays a key role in the immunomodulation of the infected host. Chronic Chagas' disease patients elicit TcTS-neutralizing antibodies that are able to inhibit the enzyme. N-Glycolylneuraminic acid has been detected in T cruzi, and the trans-sialidase was pointed out as the enzyme involved in its incorporation from host glycoconjugates. However, N-glycolylneuraminic acid alpha-(2 -> 3)-linked-containing oligosaccharides have not been analyzed as donors in the T cruzi trans-sialidase reaction. In this paper we studied the ability of TcTS to transfer N-glycolylneuraminic acid from Neu5Gc(alpha 2 -> 3)Gal(beta 1 -> 4)Glc beta OCH2CH2N3 (1) and Neu5Gc(alpha 2 -> 3) Gal(beta -> 3)GlcNAc beta OCH2CH2N3 (2) to lactitol, N-acetyllactosamine and lactose as acceptor substrates. Transfer from 1 was more efficient (50-65%) than from 2 (20-30%) for the three acceptors. The reactions were inhibited when the enzyme was preincubated with a neutralizing antibody. K-m values were calculated for 1 and 2 and compared with 3'-sialyllactose using lactitol as acceptor substrate. Analysis was performed by high-performance anion-exchange (HPAEC) chromatography. A competitive transfer reaction of compound 1 in the presence of 3'-sialyllactose and N-acetyllactosamine showed a better transfer of Neu5Gc than of Neu5Ac. (C) 2007 Elsevier Ltd. All rights reserved.
• CN116253768
  申请人：——

  公开号：——

  公开（公告）日：——
• Mass Spectrometric Analysis of Benzoylated Sialooligosaccharides and Differentiation of Terminal α2→3 and α2→6 Sialogalactosylated Linkages at Subpicomole Levels
  作者：Peng Chen、Ulrike Werner-Zwanziger、Donald Wiesler、Marty Pagel、Milos V. Novotny

  DOI：10.1021/ac990674w

  日期：1999.11.1

  Perbenzoylated sialooligosaccharides were found to be stable derivatives, giving intense signals during the matrix-assisted laser desorption/ionization (MALDI) mass spectrometric analysis in the positive-ion mode. Terminal Neu5NAcα2→3 and α2→6Gal units of oligosaccharides undergo characteristic structural changes during benzoylation, yielding easily recognizable mass spectral patterns. Subpicomole carbohydrate samples were successfully benzoylated and analyzed through MALDI mass spectrometry.

  发现过苯甲酰化唾液酸低聚糖是稳定的衍生物，在正离子模式下的基质辅助激光解吸/电离 (MALDI) 质谱分析过程中发出强烈的信号。寡糖的末端 Neu5NAcα2→3 和 α2→6Gal 单元在苯甲酰化过程中会发生特征性结构变化，产生易于识别的质谱模式。亚皮摩尔碳水化合物样品成功苯甲酰化，并通过 MALDI 质谱进行分析。