5-acetamido-3,5-dideoxy-L-glycero-D-galacto-2-nonulosonic acid | 99395-99-0

• 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-L-glycero-D-galacto-2-nonulosonic acid
• 英文别名: 7-epi-N-Acetylneuraminsaeure；sialic acid；Neu5Ac；N-acetylneuraminic acid；(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 99395-99-0
• 化学式: C₁₁H₁₉NO₉
• 分子量: 309.273
• InChiKey: SQVRNKJHWKZAKO-WKWISIMFSA-N

物化性质

• 沸点：
  805.0±65.0 °C(Predicted)
• 密度：
  1.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-acetamido-3,5-dideoxy-L-glycero-D-galacto-2-nonulosonic acid 在 氘氧化钠 、 重水 作用下， 反应 48.0h， 生成 (1R,3R,4R,5S)-1,2,2,3,5-pentamethyl-4-(2-methylallyl)-5-((2S,3R)-3-methylpentan-2-yl)-1-(prop-1-en-2-yl)cyclohexane
  参考文献：
  名称：

  通过2 H NMR光谱对区域和立体选择性氘代的唾液酸唾液酸甘油脂进行动态研究

  摘要：

  由D-甘露糖醇通过3，4-异亚丙基-D-甘露糖醇的中间体制备未标记和氘标记的[3- 2 H 1 ] 1,2-二-O-十四烷基-sn-甘油；在碱催化烯醇化下，对唾液酸进行区域和立体选择性单氘代和双氘化，得到[3ax- 2 H 1 ]-和[3ax，3eq- 2 H 2 ]-唾液酸，在衍生化后与甘油脂一起糖基化。

  DOI：

  10.1039/c39900000378
• 作为产物：
  描述：

  Methyl-4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-β-D-glycero-L-altro-2-nonulopyranosidonsaeuremethylester 在 sodium hydroxide 作用下， 反应 2.0h， 以80%的产率得到5-acetamido-3,5-dideoxy-L-glycero-D-galacto-2-nonulosonic acid
  参考文献：
  名称：

  Strukturelle Abwandlungen anN-Acetylneuramins�ure, 3

  摘要：

  DOI：

  10.1007/bf00798282

文献信息

• Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide
  作者：Ying Zhang、Fu-Long Zhao、Tao Luo、Zhichao Pei、Hai Dong

  DOI：10.1002/asia.201801486

  日期：2019.1.4

  was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2‐NPhth group and the C6‐OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth

  开发了Neu5Ac-α-2,3-LacNPhth三糖衍生物的简便方法。首先，研究了糖苷供体和葡萄糖NPhth二醇受体之间的区域/立体选择性糖基化。发现区域选择性不仅取决于葡糖胺受体的C2-NPhth基团和C6-OH保护基的空间位阻，还取决于糖苷供体的离去基团和保护基。在优化条件下，LacNPhth衍生物在高达92％的产率通过全乙酰-α-D-吡喃半乳糖三氯之间的区域选择性/立体选择性糖基化合成p -甲氧基苯基6- ö -叔-butyldiphenylsilyl -2-脱氧-2-苯二甲酰亚-β- d-吡喃葡萄糖苷，避免形成糖基化原酸酯和异头糖苷配基。然后，将LacNPhth衍生物脱酰基，然后通过TBDPS保护在伯位置上，以形成LacNPhth多元醇受体。最后，通过LacNPhth多元醇受体与亚磷酸唾液酸基酯供体之间的区域/立体选择性糖基化反应，以48％的产率合成了Neu5Ac-α-2,3-La
• Boric Acid Catalyzed Methyl Esterification of Sugar Acids
  作者：Stephan M. Levonis、Brighid B. Pappin、Alissa Sharp、Milton J. Kiefel、Todd A. Houston

  DOI：10.1071/ch13459

  日期：——

  Boric acid catalyzes methyl esterification of certain sugar acids (sialic acid, deaminated neuraminic acid) and related natural products (quinic acid) quite cleanly in some cases. However, closely related sugar acids (glucuronic acid, 3-deoxy-d-manno-oct-2-ulosonic acid) failed to esterify under the same conditions. Factors governing this dichotomy are discussed.

  硼酸在某些情况下非常干净地催化某些糖酸（唾液酸，脱氨基神经氨酸）和相关天然产物（奎宁酸）的甲基酯化。然而，密切相关的糖酸（葡糖醛酸，3-脱氧d -甘露-辛-2-糖酸）失败的相同的条件下酯化。讨论了控制这种二分法的因素。
• Synthesis of Sialidase-Resistant Oligosaccharide and Antibody Glycoform Containing α2,6-Linked 3F^ax-Neu5Ac
  作者：Hong-Jay Lo、Larissa Krasnova、Supriya Dey、Ting Cheng、Haitian Liu、Tsung-I Tsai、Kevin Binchia Wu、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/jacs.9b01991

  日期：2019.4.24

  Fluorinated glycosides are known to resist the glycosidase-catalyzed glycosidic bond cleavage; however, the synthesis of such glycans, especially 3-fluoro-sialic acid (3F-Neu5Ac) containing sialosides, has been a major challenge. Though the enzymatic synthesis of alpha-2,3-linked 3F-sialosides was reported, until recently there has not been any effective method available for the synthesis of 3F-sialosides in the a-2,6-linkage. In order to understand the biological effect of such modification, we report here a chemical synthesis of 3F(ax)-Neu5Ac-alpha 2,6-Gal as a building block for the assembly of 3Fm-Neu5Ac-containing sialosides and a representative homogeneous antibody glycoform. Our results showed that the sialosides are stable under sialidase catalysis and the rituximab glycoform with a sialylated complex-type biantennary glycan terminated with 3F(ax)-Neu5Ac in the alpha-2,6-linkage (alpha 2,6-F-SCT) has a similar binding avidity as its parent glycoform. These findings open up new opportunities for the development of therapeutic glycoproteins with improved pharmacokinetic parameters.
• Bandgar, Babasaheb P.; Hartmann, Michael; Schmid, Walther, Liebigs Annalen der Chemie, 1990, # 12, p. 1185 - 1195
  作者：Bandgar, Babasaheb P.、Hartmann, Michael、Schmid, Walther、Zbiral, Erich

  DOI：——

  日期：——
• Zbiral, Erich; Schreiner, Erwin; Salunkhe, Mamikrao M., Liebigs Annalen der Chemie, 1989, p. 519 - 526
  作者：Zbiral, Erich、Schreiner, Erwin、Salunkhe, Mamikrao M.、Schulz, Gerhard、Kleineidam, Reinhard G.、Schauer, Roland

  DOI：——

  日期：——