N-acetylneuraminic acid | 140850-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetylneuraminic acid
• 英文别名: sialic acid；(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 140850-44-8
• 化学式: C₁₁H₁₉NO₉
• 分子量: 309.273
• InChiKey: SQVRNKJHWKZAKO-MOQKELMUSA-N

物化性质

• 沸点：
  805.0±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(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：

  N-acetylneuraminic acid 在 吡啶 、 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  一种唾液酸连接吲哚菁绿Sia-ICG及其制备方法和应用

  摘要：

  本发明提供一种唾液酸连接吲哚菁绿Sia‑ICG及其制备方法和应用，属于生物医药和疾病治疗技术领域。本发明将吲哚菁绿与N‑乙酰神经氨酸通过Sia‑C9位偶联合成了Sia‑ICG。Sia‑ICG表现出良好的体外性能，具体体现在：增强稳定性，减少与血清蛋白的非特异性结合，增强生物相容性等。此外，与ICG相比，Sia‑ICG具有出色的肿瘤靶向性，且在体内的循环时间较长。重要的是，Sia‑ICG联合近红外激光照射产生了有效的光热和光动力学抗肿瘤治疗效果。因此，Sia‑ICG是极具吸引力的新一代抗癌诊疗剂，可应用于临床人类肿瘤的诊疗，因此具有良好的实际应用之价值。

  公开号：

  CN114349807A
• 作为产物：
  描述：

  5-azidopentyl 5-acetamido-3,5-dideoxy-9-O-(5-acetamido-3,5-dideoxy-9-O-(5-acetamido-3,5-dideoxy-9-O-(5-acetamido-3,5-dideoxy-9-O(5-acetamido-3,5-dideoxy-9-O-(5-acetamido-3,5-dideoxy-9-O-(5-acetamido-3,5-dideoxy-9-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galactonon-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid 在 neuraminidase 作用下， 反应 3.0h， 生成 N-acetylneuraminic acid
  参考文献：
  名称：

  有效和立体选择性合成α（2→9）低聚唾液酸：从单体到十二聚体。

  摘要：

  链帮：使用会聚嵌段合成法（参见方案）以12个步骤立体选择性地合成了α（2→9）十二烷酸。氯乙酰基保护基和磷酸基团作为离去基团的使用导致糖基化反应的α选择性的改善，从而允许合成低聚物。

  DOI：

  10.1002/anie.201101794

文献信息

• CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140235575A1

  公开（公告）日：2014-08-21

  The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

  本发明提供了一种一锅多酶法，用于从简单糖起始材料制备UDP糖。该发明还提供了一种一锅多酶法，用于从简单糖起始材料制备寡糖。
• 一种α-2,3唾液酸化乳果糖制备方法
  申请人：河南科技学院

  公开号：CN105949250B

  公开（公告）日：2018-08-31

  本发明公开了一种α‑2，3唾液酸化乳果糖制备方法，其特征在于：一定组份的乳果糖、三磷酸胞苷钠、唾液酸、溶于超纯水中，用3摩尔/升的NaOH调pH8.5，加入1摩尔/升的pH8.5的Tris‑HCl。然后将混合物放入37℃气浴振荡器中，反应18～30小时。采用硅胶薄层层析(TLC)检测反应程度，TLC展开溶剂采用正丙醇∶甲醇∶水＝5∶2∶1。待乳果糖反应完全后，往反应液中加等体积95％乙醇，混合均匀，放入4℃冰箱中静置30min，然后在7000转/分下离心30min，上清液采用旋转蒸发浓缩。浓缩液采用硅胶色谱柱纯化，再经冷冻干燥即为纯品。
• Evaluation of the antitumor effect of dexamethasone palmitate and doxorubicin co-loaded liposomes modified with a sialic acid–octadecylamine conjugate
  作者：Jing Sun、Yanzhi Song、Mei Lu、Xiangyun Lin、Yang Liu、Songlei Zhou、Yuqing Su、Yihui Deng

  DOI：10.1016/j.ejps.2016.08.029

  日期：2016.10

  Dexamethasone palmitate has the potential to inhibit the activity of tumor-associated macrophages, which promote cancer proliferation, invasion, and metastasis; however, only very high and frequent doses are capable of inducing antitumor effects. With the aim to reduce the anticancer dose and decrease the nonspecific toxicity, we designed a liposomal system to co-deliver dexamethasone palmitate and doxorubicin. Furthermore, a ligand conjugate sialic acid-octadecylamine, with enhanced affinity towards the membrane receptors over-expressed in tumors, was anchored on the surface of the liposomes to increase drug distribution to the tumor tissue. Co-loaded liposomes were developed using lipid film hydration method to load dexamethasone palmitate and remote loading technology to load doxorubicin. The co-loaded liposomes modified with sialic acid-octadecylamine represented comparable physicochemical properties and blood plasma profiles with conventional co-loaded liposomes, but the biodistribution proved that sialic acid-octadecylamine modified liposomes accumulated more in tumor. The co-loaded liposomes showed higher tumor growth suppression than the single-drug loaded liposomes, while showing no additional drug toxicity in S180-bearing Kunming mice. The co-loaded liposomes modified with sialic acid-octadecylamine achieved a significantly better antitumor effect, and induced "shedding" of cancerous tissue in the mice. These finding suggested that co-loaded liposomes modified with sialic acid-octadecylamine provided a safe therapeutic strategy with outstanding anticancer activity. (C) 2016 Elsevier B.V. All rights reserved.
• Kragl, Udo; Gygax, Daniel; Ghisalba, Oreste, Angewandte Chemie, <hi>1991</hi>, vol. 103, # 7, p. 854 - 855
  作者：Kragl, Udo、Gygax, Daniel、Ghisalba, Oreste、Wandrey, Christian

  DOI：——

  日期：——
• Efficient and Stereoselective Synthesis of α(2→9) Oligosialic Acids: From Monomers to Dodecamers
  作者：Kuo-Ching Chu、Chien-Tai Ren、Chun-Ping Lu、Che-Hsiung Hsu、Tsung-Hsien Sun、Jeng-Liang Han、Bikash Pal、Tsung-An Chao、Yung-Feng Lin、Shih-Hsiung Wu、Chi-Huey Wong、Chung-Yi Wu

  DOI：10.1002/anie.201101794

  日期：2011.9.26

  The chain gang: The α(2→9) dodecasialic acid has been stereoselectively synthesized in 12 steps by using a convergent block synthesis (see scheme). The use of chloroacetyl protecting groups and a phosphate group as a leaving group led to the improvement of the α selectivity of the glycosylation reactions, thus allowing synthesis of oligomers.

  链帮：使用会聚嵌段合成法（参见方案）以12个步骤立体选择性地合成了α（2→9）十二烷酸。氯乙酰基保护基和磷酸基团作为离去基团的使用导致糖基化反应的α选择性的改善，从而允许合成低聚物。