α-O-methyl-neuraminic acid | 57344-93-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-O-methyl-neuraminic acid
• 英文别名: methyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid；(2R,4S,5R,6R)-5-azaniumyl-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 57344-93-1
• 化学式: C₁₀H₁₉NO₈
• 分子量: 281.263
• InChiKey: OMVQZDUAKZZNEF-AVDKMFPGSA-N

物化性质

• 沸点：
  614.8±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

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

反应信息

• 作为反应物：
  描述：

  α-O-methyl-neuraminic acid 在 sialate O-acetylesterase sodium azide 、 碳酸氢铵 作用下， 以 甲醇 、 水 为溶剂， 反应 28.0h， 生成 ammonium 3,5-dideoxy-5-thioacetamido-D-glycero-D-galacto-2-nonulopyranosonate
  参考文献：
  名称：

  Synthesis of 5-N- and 9-N-thioacylated sialic acids

  摘要：

  N-Thioacylation of neuraminic acid methyl alpha-glycoside (5) with O-ethyl thioformate (1), methyl dithioacetate (2), and methyl dithiopropionate (3) afforded N-thioformyl, N-thioacetyl, and N-thiopropionyl neuraminic acid derivatives 6a-c in high yield. Cleavage of the glycosides was accomplished either by acid hydrolysis or by sialidase treatment. Alternatively, 5-N-thioacylneuraminic acids were produced from the corresponding N-thioacyl-D-mannosamines 7a-c and pyruvate employing N-acetylneuraminate pyruvate lyase. The sialidase-resistant methyl alpha-thioglycoside of N-thioacetylneuraminic acid (10) was also prepared. N-Acetyl-9-deoxy-9-thioacetamido neuraminic acid (19) was obtained either directly by reaction of N-acetyl-9-amino-9-deoxyneuraminic acid (17) with methyl dithioacetate (2) or via its methyl alpha-glycoside 18. Compound 17 was produced from the methyl a-glycoside of 9-O-tosylated methyl ester 12 via the azide 13. -For the 5-N-thioacyl sialic acids 6a-c and 8a-c as well as for the 9-deoxy-9-thioacetamido derivatives 18 and 19 some biological properties are reported.

  DOI：

  10.1016/s0040-4020(01)90473-9
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 水 、 乙酰氯 、 三氟乙酸 、 sodium hydroxide 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 生成 α-O-methyl-neuraminic acid
  参考文献：
  名称：

  Differential Recognition of Diet-Derived Neu5Gc-Neoantigens on Glycan Microarrays by Carbohydrate-Specific Pooled Human IgG and IgA Antibodies

  摘要：

  硅烷酸（Sias）覆盖脊椎动物细胞表面的聚糖。N-乙酰神经氨酸（Neu5Ac）及其羟化形式 N-乙酰神经氨酸（Neu5Gc）是哺乳动物常见的 Sia。人类不能合成 Neu5Gc，但通过富含红色肉类的饮食将其积累在细胞上，产生了大量具有免疫原性的 Neu5Gc-新抗原。因此，人类产生了多种抗 Neu5Gc 抗体，影响了异种移植、癌症、动脉粥样硬化和不孕症。抗 Neu5Gc 抗体以 IgG、IgM 和 IgA 三种异型循环存在；然而，目前还没有对大量人群中不同异型抗体的复合物进行研究。在这里，我们使用聚糖微阵列分别研究了静脉注射免疫球蛋白（IVIG）或集合人类 IgA 中的抗 Neu5Gc IgG 和 IgA。用 Neu5Gc 和 Neu5Ac 聚糖制作的微阵列上的结合模式以及抑制测定显示，不同的 IVIG 制剂具有高度特异性的抗 Neu5Gc IgG 反应，其反应谱密切相关，而 IgA 则对几种 Neu5Ac 聚糖表现出交叉反应。个体中这种不同的抗 Neu5Gc IgG/IgA 反应谱可能会对人类疾病产生不同的影响。

  DOI：

  10.1021/acs.bioconjchem.9b00273

文献信息

• Synthesis of potential inhibitors of hemagglutination by influenza virus: chemoenzymic preparation of N-5 analogs of N-acetylneuraminic acid.
  作者：Michelle A. Sparks、Kevin W. Williams、Christine Lukacs、Andreas Schrell、Gregory Priebe、Andreas Spaltenstein、George M. Whitesides

  DOI：10.1016/s0040-4020(01)80502-0

  日期：1993.1

  A chemoenzymic route to neuraminic acid 2 is described. This method is based on conversion of N-carbobenzoxymannosamine (ManCBz) 3 to N-carbobenzoxyneuraminic acid (Neu5CBz) 4, catalyzed by Neu5Ac aldolase. The Neu5CBz 4 was converted to the α-methyl glycoside 8 and deprotected to afford the free amine 2. This procedure has been scaled up to generate 10-gram quantities of 2. N-Acylation of 2 produced

  描述了向神经氨酸2的化学酶途径。该方法基于由Neu5Ac醛缩酶催化的N-碳代苯甲氧基甘露糖胺（ManCBz）3到N-碳代苯并神经氨酸（Neu5CBz）4的转化。Neu5CBz 4转化为α-甲基糖苷8并脱保护得到游离胺2。此过程已按比例放大以生成10克数量的2。的N-酰化2产生几个新的N-酰基神经氨酸类似物; 在血凝抑制试验（HAI）中，已将它们评估为流感病毒与鸡红细胞粘附的抑制剂。神经氨酸2的这种制备 与其他文献程序进行比较。
• Synthesis of Oligomers Derived from Amide-Linked Neuraminic Acid Analogues
  作者：Travis Q. Gregar、Jacquelyn Gervay-Hague

  DOI：10.1021/jo035312+

  日期：2004.2.1

  N-Fluoren-9-ylmethoxycarbonyl-protected sugar amino acids derived from α-O-methoxy- and 2,3-dehydroneuraminic acids have been prepared. Incorporation of these monomer units into solid-phase synthesis led to the efficient synthesis of two series of oligomers varying from one to eight units in length. The (1→5)-linked amides of 2,3-dehydroneuraminic acid were further subjected to hydrogenation giving a

  已经制备了由α - O-甲氧基-和2，3-脱氢尿嘧啶酸衍生的N-氟人-9-基甲氧基羰基保护的糖氨基酸。将这些单体单元结合到固相合成中导致有效合成长度从一到八个单元的两个系列的低聚物。将2，3-脱氢尿嘧啶酸的（1→5）-连接的酰胺进一步进行氢化，得到在异头碳处具有β-氢取代基的第三系列低聚物。
• Differential Recognition of Diet-Derived Neu5Gc-Neoantigens on Glycan Microarrays by Carbohydrate-Specific Pooled Human IgG and IgA Antibodies
  作者：Shani Leviatan Ben-Arye、Christoph Schneider、Hai Yu、Salam Bashir、Xi Chen、Stephan von Gunten、Vered Padler-Karavani

  DOI：10.1021/acs.bioconjchem.9b00273

  日期：2019.5.15

  Sialic acids (Sias) cover vertebrate cell surface glycans. N-Acetylneuraminic acid (Neu5Ac) and its hydroxylated form N-glycolylneuraminic acid (Neu5Gc) are common Sia in mammals. Humans cannot synthesize Neu5Gc but accumulate it on cells through red-meat rich diets, generating numerous immunogenic Neu5Gc-neoantigens. Consequently, humans have diverse anti-Neu5Gc antibodies affecting xenotransplantation, cancer, atherosclerosis, and infertility. Anti-Neu5Gc antibodies circulate as IgG, IgM, and IgA isotypes; however, repertoires of the different isotypes in a large population have not been studied yet. Here, we used glycan microarrays to investigate anti-Neu5Gc IgGs and IgAs in intravenous immunoglobulin (IVIG) or pooled human IgA, respectively. Binding patterns on microarrays fabricated with Neu5Gc- and Neu5Ac-glycans, together with inhibition assays, revealed that different IVIG preparations have highly specific anti-Neu5Gc IgG reactivity with closely related repertoires, while IgAs show cross-reactivity against several Neu5Ac-glycans. Such different anti-Neu5Gc IgG/IgA repertoires in individuals could possibly mediate distinctive effects on human diseases.

  硅烷酸（Sias）覆盖脊椎动物细胞表面的聚糖。N-乙酰神经氨酸（Neu5Ac）及其羟化形式 N-乙酰神经氨酸（Neu5Gc）是哺乳动物常见的 Sia。人类不能合成 Neu5Gc，但通过富含红色肉类的饮食将其积累在细胞上，产生了大量具有免疫原性的 Neu5Gc-新抗原。因此，人类产生了多种抗 Neu5Gc 抗体，影响了异种移植、癌症、动脉粥样硬化和不孕症。抗 Neu5Gc 抗体以 IgG、IgM 和 IgA 三种异型循环存在；然而，目前还没有对大量人群中不同异型抗体的复合物进行研究。在这里，我们使用聚糖微阵列分别研究了静脉注射免疫球蛋白（IVIG）或集合人类 IgA 中的抗 Neu5Gc IgG 和 IgA。用 Neu5Gc 和 Neu5Ac 聚糖制作的微阵列上的结合模式以及抑制测定显示，不同的 IVIG 制剂具有高度特异性的抗 Neu5Gc IgG 反应，其反应谱密切相关，而 IgA 则对几种 Neu5Ac 聚糖表现出交叉反应。个体中这种不同的抗 Neu5Gc IgG/IgA 反应谱可能会对人类疾病产生不同的影响。
• Synthesis of 5-N- and 9-N-thioacylated sialic acids
  作者：Rainer Isecke、Reinhard Brossmer

  DOI：10.1016/s0040-4020(01)90473-9

  日期：——

  N-Thioacylation of neuraminic acid methyl alpha-glycoside (5) with O-ethyl thioformate (1), methyl dithioacetate (2), and methyl dithiopropionate (3) afforded N-thioformyl, N-thioacetyl, and N-thiopropionyl neuraminic acid derivatives 6a-c in high yield. Cleavage of the glycosides was accomplished either by acid hydrolysis or by sialidase treatment. Alternatively, 5-N-thioacylneuraminic acids were produced from the corresponding N-thioacyl-D-mannosamines 7a-c and pyruvate employing N-acetylneuraminate pyruvate lyase. The sialidase-resistant methyl alpha-thioglycoside of N-thioacetylneuraminic acid (10) was also prepared. N-Acetyl-9-deoxy-9-thioacetamido neuraminic acid (19) was obtained either directly by reaction of N-acetyl-9-amino-9-deoxyneuraminic acid (17) with methyl dithioacetate (2) or via its methyl alpha-glycoside 18. Compound 17 was produced from the methyl a-glycoside of 9-O-tosylated methyl ester 12 via the azide 13. -For the 5-N-thioacyl sialic acids 6a-c and 8a-c as well as for the 9-deoxy-9-thioacetamido derivatives 18 and 19 some biological properties are reported.