5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonamide | 35290-33-6

• 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-D-glycero-β-D-galacto-non-2-ulopyranosonamide
• 英文别名: N-acetyl-beta-neuraminamide；(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxamide
• CAS: 35290-33-6
• 化学式: C₁₁H₂₀N₂O₈
• 分子量: 308.288
• InChiKey: PKSULYZGXFBQIQ-PFQGKNLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 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：
  183
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonamide 、 乙酸酐 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Efficient Synthesis of MUC4 Sialylglycopeptide through the New Sialylation Using 5-Acetamido-Neuraminamide Donors

  摘要：

  Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy2-O-beta-D-glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-l-amide-2-phosphite) derivatives, and the synthesis of the sialyl-T-N-MUC4 glycopeptide are described. The sialylation was performed in CH2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated alpha-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-alpha(2,6)-GalN(3) was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-T-N serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-T-N serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-T-N-MUC4 glycopeptide.

  DOI：

  10.1021/jo702609p
• 作为产物：
  描述：

  N-乙酰神经氨酸甲酯 在 ammonium hydroxide 、 碳酸氢铵 作用下， 反应 1.0h， 以91%的产率得到5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonamide
  参考文献：
  名称：

  Efficient Synthesis of MUC4 Sialylglycopeptide through the New Sialylation Using 5-Acetamido-Neuraminamide Donors

  摘要：

  Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy2-O-beta-D-glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-l-amide-2-phosphite) derivatives, and the synthesis of the sialyl-T-N-MUC4 glycopeptide are described. The sialylation was performed in CH2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated alpha-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-alpha(2,6)-GalN(3) was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-T-N serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-T-N serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-T-N-MUC4 glycopeptide.

  DOI：

  10.1021/jo702609p

文献信息

• Gangliosides containing de-N-acetyl-sialic acid and their applications as modifiers of cell physiology
  申请人：The Biomembrane Institute

  公开号：EP0328420A2

  公开（公告）日：1989-08-16

  Substantially pure gangliosides containing de-N-acetyl-sialic acid. A culture medium for stimulating growth of human and animal cells comprising: (1) essential nutrients for cell growth, and (2) a cell growth stimulatory amount of one or more gangliosides containing de-N-acetyl-sialic acid. A method for stimulating growth of human and animal cells cultured in vitro comprising contacting said cells in culture with a cell growth stimulatory amount of one or more gangliosides containing de-N-acetyl-sialic acid. A medicament for stimulating growth of human and animal cells comprising: (1) a cell growth stimulatory amount of one or more growth stimulators selected from the group consisting of gangliosides containing de-N-acetyl-sialic acid, substances that promote synthesis of gangliosides containing de-N-acetyl-sialic acid and pharmaceutically acceptable salts thereof; and (2) a pharmaceutically acceptable carrier, diluent or excipient. A method for stimulating growth of human and animal cells in vivo comprising contacting said cells with a cell growth stimulatory amount of gangliosides containing de-N-acetyl-sialic acid, substances that promote synthesis of gangliosidea containing de-N-acetyl-sialic acid, and pharmaceutically acceptable salts thereof. A medicament for inhibiting growth of human and animal cells comprising: (1) a cell growth inhibitory amount of one or more growth inhibitors that block synthesis of gangliosides containing de-N-acetyl-sialic acid or pharmaceutically acceptable salts thereof; and (2) a pharmaceutically acceptable carrier, diluent or excipient. A method for inhibiting growth of human and animal cells in vivo comprising contacting said cells with a cell growth inhibitory amount of one or more growth inhibitors that block synthesis of gangliosides containing de-N-acetyl-sialic acid or pharmaceutically acceptable salts thereof.

  含有脱-N-乙酰基-神经节苷脂的纯度很高的神经节苷脂。一种刺激人类和动物细胞生长的培养基，包括：(1) 细胞生长所必需的营养物质；(2) 一种或多种含有去 N-乙酰基-麸酸的神经节苷脂的细胞生长刺激物。一种刺激体外培养的人类和动物细胞生长的方法，包括使培养细胞与一种或多种含有去 N-乙酰基-麸酸的神经节苷脂的细胞生长刺激量接触。一种刺激人和动物细胞生长的药物，包括：(1) 一种或多种刺激细胞生长的生长剂，这些生长剂选自含有去 N-乙酰基-sialic酸的神经节苷脂、促进合成含有去 N-乙酰基-sialic酸的神经节苷脂的物质及其药学上可接受的盐组成的组；(2) 药学上可接受的载体、稀释剂或赋形剂。一种刺激体内人和动物细胞生长的方法，包括使所述细胞与刺激细胞生长量的含去 N-乙酰基-sialic酸的神经节苷脂、促进合成含去 N-乙酰基-sialic酸的神经节苷脂的物质及其药学上可接受的盐接触。一种抑制人和动物细胞生长的药物，包括：(1) 一种或多种生长抑制剂的细胞生长抑制量，该生长抑制剂可阻断含有去 N-乙酰基-ialic酸的神经节苷脂或其药学上可接受的盐的合成；(2) 药学上可接受的载体、稀释剂或赋形剂。一种抑制体内人和动物细胞生长的方法，包括使所述细胞与一种或多种生长抑制剂接触，该生长抑制剂具有细胞生长抑制量，可阻断含有脱-N-乙酰基-sialic acid 的神经节苷脂或其药学上可接受的盐的合成。
• Methods of preparing de-N-acylated and N-acylated glycospingo lipids and lyso forms of glycospingo lipids
  申请人：The Biomembrane Institute

  公开号：EP0332298A2

  公开（公告）日：1989-09-13

  A method for preparing de-N-acylated forms of an N-acyl sugar-containing glycospingolipid comprising hydrolyzing the glycospingolipids under mild alkaline conditions such that the N-acyl group of the sugar moiety is preferentially hydrolyzed. A method for preparing N-acylated forms of an amino sugar-containing lyso form glycospingolipid comprising protecting the amino group of the spingosine by incorporating the glycospingolipid into a phospholipid or hydrophobic matrix and then conducting selective N-acylation on the amino group of the sugar moiety. Methods for preparing labeled glycospingolipids also disclosed.

  一种制备去 N-酰化形式的含 N-酰基糖的糖磷脂的方法，包括在弱碱性条件下水解糖磷脂，使糖分子的 N-酰基优先水解。一种制备含氨基糖的溶菌型糖磷脂的 N-酰化形式的方法，包括通过将糖磷脂加入磷脂或疏水基质中来保护刺五加的氨基，然后对糖分子的氨基进行选择性 N-酰化。还公开了制备标记糖磷脂的方法。
• Modified gangliosides and the functional derivatives thereof
  申请人：FIDIA S.p.A.

  公开号：EP0433112A1

  公开（公告）日：1991-06-19

  N-acyl-N,N′-di-lysogangliosides, N′-acyl-N,N′-di-­lysogangliosides and N,N′-diacyl-N,N′-di-­lysogangliosides, in which the acyl groups are derived from an organic acid of the aliphatic, aromatic, araliphatic, alicyclic or heterocyclic series and in which at least one of the two acyl groups is not aliphatic, and their preparation are disclosed. Also disclosed is the preparation of the esters, inner esters, amides and hydroxy peracylates of these compounds and salts thereof. These compounds are useful in the treatment of pathologies of the central and peripheral nervous systems.

  N-acyl-N,N′-di-lysogangliosides, N′-acyl-N,N′-di-lysogangliosides和N,N′-diacyl-N,N′-di-lysogangliosides，其中酰基来自脂肪族、芳香族、脂环族、脂环族或杂环族的有机酸，并且其中至少有一个酰基不是脂肪族、本发明公开了两个酰基中至少有一个不是脂肪族的二乙酰基-N，N′-二赖糖糖苷及其制备方法。此外，还公开了这些化合物的酯、内酯、酰胺和羟基过酰基化合物及其盐的制备方法。这些化合物可用于治疗中枢和外周神经系统的疾病。
• Semisynthetic ganglioside analogues
  申请人：FIDIA S.p.A.

  公开号：EP0410881B1

  公开（公告）日：1997-09-17
• Di-lysogangliosides derivatives
  申请人：FIDIA S.p.A.

  公开号：EP0410883B1

  公开（公告）日：1999-03-31