beta-神经氨酸甲酯 | 56144-08-2

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-神经氨酸甲酯
• 中文别名: 神經胺[糖]酸
• 英文名称: 5-amino-O²-methyl-β-D-glycero-D-galacto-3,5-dideoxy-[2]nonulopyranosonic acid
• 英文别名: 5-Amino-O²-methyl-β-D-glycero-D-galacto-3,5-didesoxy-[2]nonulopyranosonsaeure；Methyl 5-amino-3,5-dideoxy-D-glycero-beta-D-galacto-2-nonulopyranosidonic acid；(2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 56144-08-2
• 化学式: C₁₀H₁₉NO₈
• mdl: MFCD00057552
• 分子量: 281.263
• InChiKey: OMVQZDUAKZZNEF-APDUKXCWSA-N

物化性质

• 熔点：
  Softens and Yellows at 150°C; 200°C dec.
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 储存条件：
  -20°C冷冻存储，置于惰性气体氛围下

制备方法与用途

用途
这是一种合成中间体，用于制备氨基连接的糖胺聚糖。它是一种天然存在的Δ9-氨基酸。

反应信息

• 作为反应物：
  描述：

  beta-神经氨酸甲酯 在 吡啶 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 44.0h， 生成 (2S,4S,5R,6R)-4-acetyloxy-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Solid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers¹

  摘要：

  A series of dimeric through octameric (1-->5) amid-linked sialooligomers were prepared using solid-phase peptide methods on Rink resin with Fmoc protecting group chemistry. The oligomers were conjugated to epsilon-amino caproic acid in order to model membrane-bound conformations. The secondary structure of the oliogomers was probed with NH/ND exchange rates determined by NMR, and with circular dichroism. The combined structural studies show that a tetramer is required for ordered secondary structure, and that secondary structure is stabilized upon elongation to pentameric and hexameric species. Interestingly, the heptamer shows rapid NH/ND exchange rates; however, ordered secondary structure is restored in the octamer. These studies provide the first evidence that oligomers composed of constrained carbohydrate-derived amino acids form stable secondary structures in water.

  DOI：

  10.1021/jo971415e
• 作为产物：
  描述：

  N-乙酰神经氨酸 在 盐酸 、 甲醇 作用下， 生成 beta-神经氨酸甲酯
  参考文献：
  名称：

  Klenk; Faillard, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1954, vol. 297, p. 230,238

  摘要：

  DOI：

文献信息

• Charon, Daniel; Szabo, Ladislas; Cesario, Michele, Journal of the Chemical Society. Perkin transactions I, 1982, # 12, p. 3055 - 3064
  作者：Charon, Daniel、Szabo, Ladislas、Cesario, Michele、Guilhem, Jean

  DOI：——

  日期：——
• Klenk et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1956, vol. 304, p. 35,38
  作者：Klenk et al.

  DOI：——

  日期：——
• Solid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers¹
  作者：Lajos Szabo、Brenda L. Smith、Katherine D. McReynolds、Abby L. Parrill、Edwin R. Morris、Jacquelyn Gervay

  DOI：10.1021/jo971415e

  日期：1998.2.1

  A series of dimeric through octameric (1-->5) amid-linked sialooligomers were prepared using solid-phase peptide methods on Rink resin with Fmoc protecting group chemistry. The oligomers were conjugated to epsilon-amino caproic acid in order to model membrane-bound conformations. The secondary structure of the oliogomers was probed with NH/ND exchange rates determined by NMR, and with circular dichroism. The combined structural studies show that a tetramer is required for ordered secondary structure, and that secondary structure is stabilized upon elongation to pentameric and hexameric species. Interestingly, the heptamer shows rapid NH/ND exchange rates; however, ordered secondary structure is restored in the octamer. These studies provide the first evidence that oligomers composed of constrained carbohydrate-derived amino acids form stable secondary structures in water.
• Klenk; Faillard, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1954, vol. 297, p. 230,238
  作者：Klenk、Faillard

  DOI：——

  日期：——