(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-hexadecanamino-4-octadecene-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-hexadecanamino-4-octadecene-1,3-diol
• 英文别名: alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/16:0)；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(E,2S,3R)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-enoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₅₇H₁₀₄N₂O₂₁
• 分子量: 1153.45
• InChiKey: NURCPIMQAUMKKZ-ORNMTBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  80
• 可旋转键数：
  43
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  373
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  N-乙酰神经氨酸水合物 在 CMP-唾液酸合成酶 、 pasteurella multocida multifunctional α2–3-sialyltransferase 3 、 碳酸氢钠 、 胞苷-5’-三磷酸 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-hexadecanamino-4-octadecene-1,3-diol
  参考文献：
  名称：

  简化的优先神经节苷脂癌症抗原化学化学全合成

  摘要：

  展示了一种高效的简化化学酶策略，可从市售乳糖和植物鞘氨醇中合成四种优先神经节苷脂类癌抗原GD2，GD3，岩藻糖基GM1和GM3。化学合成了乳糖基鞘氨醇（LacβSph）（13 g规模），进行了连续一锅多酶（OPME）糖基化反应，并进行了简便的C18碳粉纯化，然后改善了酰化条件，形成了目标神经节苷脂，包括岩藻糖基GM1，以前从未合成过。

  DOI：

  10.1039/c8ob01087k

文献信息

• The total synthesis of ganglioside GM3
  作者：Richard I. Duclos

  DOI：10.1016/s0008-6215(00)00121-x

  日期：2000.10

  beta-Gal-(1'' --> 3'/4')-GlcNAc alpha-(2''' --> 3'')-sialyltransferase enzyme, and was evaluated as a synthetic intermediate to ganglioside GM3. The chemical total synthesis of ganglioside GM3 was performed on one of the largest scales yet reported. The highlights of this synthesis include minimizing the steps necessary to prepare the lactosyl acceptor as a useful anomeric mixture, which was present in

  审查了神经节苷脂GM3（NeuAc alpha3Gal beta4Glc beta1Cer）的先前合成，并研究了化学酶和化学全合成方法。在化学酶学方法中，（2S，3R，4E）-5'''-乙酰基-α-神经氨酸-（2'''-> 3''）-β-吡喃半乳糖基-（1''-> 4'使用重组β-Gal-（1''-> 3'可以轻松制备）-β-吡喃葡萄糖基-（1'-> 1）-2-叠氮基-4-十八碳烯1，，3-二醇（azidoGM3） / 4'）-GlcNAcα-（2'''-> 3''）-唾液酸转移酶，被评估为神经节苷脂GM3的合成中间体。神经节苷脂GM3的化学全合成以迄今报道的最大规模之一进行。该合成的亮点包括最小化制备作为有用的异头混合物的乳糖基受体所必需的步骤，对于与已知神经氨酰基供体的高度区域选择性和相当立体选择性的唾液酸化，过量存在以得到被保护的GM3三糖。合成方法通过充分表征的GM3三糖三氯乙亚氨
• Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains
  作者：Hai Yu、Madhusudhan Reddy Gadi、Yuanyuan Bai、Libo Zhang、Lei Li、Jun Yin、Peng G. Wang、Xi Chen

  DOI：10.1021/acs.joc.1c00450

  日期：2021.7.2

  diverse GM3 gangliosides containing various sialic acid forms and different fatty acyl chains in low cost, an improved process was developed to chemically synthesize lactosyl sphingosine from an inexpensive l-serine derivative. It was then used to obtain GM3 sphingosines from diverse modified sialic acid precursors by an efficient one-pot multienzyme sialylation system containing Pasteurella multocida

  神经节苷脂是一种含唾液酸的鞘糖脂，已在所有脊椎动物的细胞膜中发现。它们的重要生物学功能由聚糖和神经酰胺脂质成分共同贡献。GM3 是一种主要的神经节苷脂，也是许多其他更复杂的神经节苷脂的前体。为了以低成本获得结构多样的含有各种唾液酸形式和不同脂肪酰基链的 GM3 神经节苷脂，开发了一种改进的工艺，以从廉价的l-丝氨酸衍生物化学合成乳糖基鞘氨醇。然后将其用于通过有效的一锅多酶唾液酸化系统从多种修饰的唾液酸前体中获得 GM3 鞘氨醇，该系统含有多杀性巴氏杆菌唾液酸转移酶 3 (PmST3 )糖核苷酸的产生。然后使用高效的化学酰化和简便的 C18 滤芯纯化工艺来安装不同长度和不同修饰的脂肪酰基链。化学酶法代表了一种强大的全合成策略，可以访问结构定义的 GM3 神经节苷脂库以探索其功能。
• Glycosynthase-Mediated Synthesis of Glycosphingolipids
  作者：Mark D. Vaughan、Karl Johnson、Shawn DeFrees、Xiaoping Tang、R. Antony J. Warren、Stephen G. Withers

  DOI：10.1021/ja058469n

  日期：2006.5.1

  Glycosphingolipids play crucial roles in virtually every stage of the cell cycle, and their clinical administration has been proposed as a treatment for Alzheimer's, Parkinson's, stroke, and a range of other conditions. However, lack of supply has severely hindered testing of this potential. A novel glycosynthase-based synthetic strategy is demonstrated, involving a mutant of an endoglycoceramidase in which the catalytic nucleophile has been ablated. This mutant efficiently couples a range of glycosyl fluoride donors with a range of sphingosine-based acceptors in yields around 95%. This technology opens the door to large-scale production of glycosphingolipids and, thus, to clinical testing.
• Synthetic Studies on Sialoglycoconjugates 89: Synthesis of Ganglioside GM₃and KDN-GM₃Containing Different Carbon-Chain Length Fatty Acyl Groups at the Ceramide Residue
  作者：Akira Hasegawa、Naomi Suzuki、Fumitaka Kozawa、Hideharu Ishida、Makoto Kiso

  DOI：10.1080/07328309608005680

  日期：1996.7

  Ganglioside GM(3) and KDN-ganglioside GM(3), containing hexanoyl, decanoyl, and hexadecanoyl groups at the ceramide moiety have been synthesized. Selective reduction of the azido group in O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D -gIycero-alpha-D-galacro-2-nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl) (1-->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-beta-D-glucopyranosyl)-(1-->1)-(2S,3R,4E)-2-azid-3-O-benzoyl-4-octadecene-1,3-diol (1) and O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-gIycero-alpha-D-galacto-2- nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-beta-D-glucopyranosyl)-(1-->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene- 1,3-diol (2), coupling with hexanoic, decanoic, and hexadecanoic acids, O-deacylation, and de-esterification gave the title gangliosides GM(3) (11 similar to 13) and KDN-GM(3) (14 similar to 16) in good yields. On the other hand, O-deacylation of 1 and subsequent de-esterification gave 2-azido-sphingosine containing-GM(3) analogue 17, which was converted into lyso-GM(3), in which no fatty acyl group was substituted at the sphingosine residue, by selective reduction of the azido group.
• Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens
  作者：Hai Yu、Abhishek Santra、Yanhong Li、John B. McArthur、Tamashree Ghosh、Xiaoxiao Yang、Peng G. Wang、Xi Chen

  DOI：10.1039/c8ob01087k

  日期：——

  A highly efficient streamlined chemoenzymatic strategy for total synthesis of four prioritized ganglioside cancer antigens GD2, GD3, fucosyl GM1, and GM3 from commercially available lactose and phytosphingosine is demonstrated. Lactosyl sphingosine (LacβSph) was chemically synthesized (on a 13 g scale), subjected to sequential one-pot multienzyme (OPME) glycosylation reactions with facile C18-cartridge

  展示了一种高效的简化化学酶策略，可从市售乳糖和植物鞘氨醇中合成四种优先神经节苷脂类癌抗原GD2，GD3，岩藻糖基GM1和GM3。化学合成了乳糖基鞘氨醇（LacβSph）（13 g规模），进行了连续一锅多酶（OPME）糖基化反应，并进行了简便的C18碳粉纯化，然后改善了酰化条件，形成了目标神经节苷脂，包括岩藻糖基GM1，以前从未合成过。