methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-manno-nononate | 132591-09-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-manno-nononate
• 英文别名: (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4-acetoxy-6-allyl-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyltriacetate；methyl 2-C-allyl-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-5-N-acetamido-D-glycero-α-D-galacto-nononate；methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-prop-2-enyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 132591-09-4
• 化学式: C₂₃H₃₃NO₁₂
• 分子量: 515.515
• InChiKey: JEDWQBZJXPPWQV-CFPLAWGXSA-N

物化性质

• 沸点：
  587.2±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-manno-nononate 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 甲醇 、 aluminum (III) chloride 、 硼烷-三甲胺络合物 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 (E)-methyl 5-acetamido-2,6-anhydro-9-O-benzyl-3,5-dideoxy-2-C-(3-phenylprop-2-enyl)-D-erythro-L-manno-nononate
  参考文献：
  名称：

  Sialic acid C-glycosides with aromatic residues: Investigating enzyme binding and inhibition of Trypanosoma cruzi trans-sialidase

  摘要：

  通过交叉复分解及进一步的衍生化合成，得到了几种α构型的C-唾液酸苷，作为锥虫锥体变形虫（Trypanosoma cruzi）的转运唾液酸酶（TcTS）的配体，TcTS是查加斯病中的关键酶。我们利用表面等离子共振（SPR）技术测定了这些化合物与固定化TcTS间的亲和力，所得到的KD值处于较低的毫摩尔范围内，将进行讨论。结果显示，在以靶点为导向的配体合成中，考虑到TcTS的酪氨酸119和色氨酸312侧链的重要性，因为这些氨基酸构成了TcTS活性位点的受体结合区域。在基于核磁共振的初步抑制试验中，最佳配体显著降低了TcTS的活性。

  DOI：

  10.1039/c0ob01176b
• 作为产物：
  描述：

  Methyl 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 在 偶氮二异丁腈 作用下， 以 四氢呋喃 为溶剂， 反应 44.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-manno-nononate
  参考文献：
  名称：

  Paulsen, Hans; Matschulat, Peter, Liebigs Annalen der Chemie, 1991, # 5, p. 487 - 495

  摘要：

  DOI：

文献信息

• A glycal-based photoaffinity probe that enriches sialic acid binding proteins
  作者：Peter S. Thuy-Boun、Dennis W. Wolan

  DOI：10.1016/j.bmcl.2019.07.054

  日期：2019.9

  identify sialic acid binding proteins from complex proteomes, three photocrosslinking affinity-based probes were constructed using Neu5Ac (5 and 6) and Neu5Ac2en (7) scaffolds. Kinetic inhibition assays and Western blotting revealed the Neu5Ac2en-based 7 to be an effective probe for the labeling of a purified gut microbial sialidase (BDI_2946) and a purified human sialic acid binding protein (hCD33)

  为了从复杂的蛋白质组中鉴定唾液酸结合蛋白，使用Neu5Ac（5和6）和Neu5Ac2en（7）支架构建了三个基于光交联亲和力的探针。动力学抑制分析和蛋白质印迹表明，基于Neu5Ac2en的7是标记纯化的肠道微生物唾液酸酶（BDI_2946）和纯化的人类唾液酸结合蛋白（hCD33）的有效探针。此外，基于LC-MS / MS亲和力的蛋白质谱分析证实了7能够从人血清中富集低丰度唾液酸结合蛋白（补体因子H）的能力，从而在复杂的情况下验证了该探针的实用性。
• Synthesis and inhibitory activity of sialic acid derivatives targeted at viral sialate-O-acetylesterases
  作者：Mathew Stanley、Juliane Mayr、Wolfgang Huber、Reinhard Vlasak、Hansjörg Streicher

  DOI：10.1016/j.ejmech.2011.04.008

  日期：2011.7

  A series of sialosides modified at the 4- and 9-hydroxy group were synthesised and tested for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses. While no inhibition of the sialate-4-O-acetylesterases from mouse hepatitis virus strain S or sialodacryoadenitis virus was found, a 9-O-methyl derivative displayed inhibitory activity against recombinant sialate-9-O-acetylesterase from influenza C virus. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates
  作者：Riku Ogasahara、Shuay Abdullayev、Vikram A. Sarpe、Appi Reddy Mandhapati、David Crich

  DOI：10.1016/j.carres.2020.108100

  日期：2020.10

  The adamantanyl thioglycosides of 5-isothiocyano and 5-azido 5-desamino-4,7,8,9-tetra-O-acetylneuraminic acid methyl ester were converted into the corresponding dibutyl phosphates, which proved to be excellent alpha-selective donors for O-sialidation with a range of typical acceptors, and good donors for reaction with allyltributylstannane, albeit without significant anomeric selectivity. In the KDN series the dibuylphosphate derived from a donor carrying a 4,5-cyclic carbonate protecting group afforded the corresponding C-glycoside with excellent alpha-selectivity on activation in the presence of allyltributylstannane, whereas the corresponding donor carrying acetate esters at the 4and 5-positions was unselective. Overall, it is revealed that while the strongly electron-withdrawing isothiocyanato and azido groups are sufficient to promote highly alpha-selective O-sialidation, they are inadequate when faced with less reactive nucleophiles when mixtures of anomers are obtained.
• Cross metathesis for the synthesis of novel C-sialosides
  作者：Sebastian Meinke、Joachim Thiem

  DOI：10.1016/j.carres.2008.03.036

  日期：2008.7

  Cross metathesis of both anomers of C-allyl sialoside (3 alpha/3 beta) with styrene catalyzed by the second generation Grubbs or Hoveyda-Grubbs catalysts gave the corresponding aryl derivatives (4 alpha/4 beta) in virtually quantitative yields. The products were hydrogenated to model compounds 5 alpha/5 beta. Similarly, reaction of the alpha-anomer 3 alpha with galactose derivative 8 gave the olefin-linked disaccharide mimetic 9. Following hydrogenation and deprotection, the ethylene-bridged Neu5Ac alpha(2 -> 6)Gal analogue 11 could be obtained. (c) 2008 Elsevier Ltd. All rights reserved.
• PAULSEN, HANS;MATSCHULAT, PETER, LIEBIGS ANN. CHEM.,(1991) N, C. 487-495
  作者：PAULSEN, HANS、MATSCHULAT, PETER

  DOI：——

  日期：——