5-acetamido-2-O-acetyl-3,5-dideoxy-D-glycero-D-galactononulopyranosic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-2-O-acetyl-3,5-dideoxy-D-glycero-D-galactononulopyranosic acid
• 英文别名: O-acetyl sialic acid；b-NeuAc2Ac；(2R,4S,5R,6R)-5-acetamido-2-acetyloxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₁₃H₂₁NO₁₀
• 分子量: 351.31
• InChiKey: KSZGNGMDMORQFX-GRRZBWEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 对甲苯磺酸 、 溶剂黄146 、 三甲基氢氧化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 149.0h， 生成 5-acetamido-2-O-acetyl-3,5-dideoxy-D-glycero-D-galactononulopyranosic acid
  参考文献：
  名称：

  完整的系列的单乙酸盐的合成Ñ乙酰基d -neuraminic酸†

  摘要：

  每种单乙酸盐的简短合成 N-乙酰基-D-神经氨酸被报道。这些是研究利用Neu5Ac作为底物的酶的机制和功能的重要分子。但是，直到现在，这些分子还不能以纯化合物形式获得，而是必须以混合物形式进行研究。Neu4,5Ac 2和Neu5,8Ac 2分别从一个普通的前体分2步和4个步骤合成，而Neu2,4Ac 2和Neu5,7Ac 2分别从另一个普通的前体分3个步骤和4个步骤合成。从Neu5Ac本身可以很容易地通过3个步骤制备两种前体。重要的是，在这些合成的整个过程中都没有检测到异头立体化学的混乱。

  DOI：

  10.1039/c1ob06348k

文献信息

• [EN] SACCHARIDE DERIVATIVE OF A TOXIC PAYLOAD AND ANTIBODY CONJUGATES THEREOF<br/>[FR] DÉRIVÉ DE SACCHARIDE D'UNE CHARGE UTILE TOXIQUE ET CONJUGUÉS D'ANTICORPS DE CELUI-CI
  申请人：GLYKOS FINLAND OY

  公开号：WO2016001485A1

  公开（公告）日：2016-01-07

  A molecule comprising a saccharide bound via an O- glycosidic bond to a hydroxyl group of a toxic payload molecule is disclosed. An antibody-drug conjugate comprising an antibody covalently bound to a toxic payload molecule, optionally via a linker group,and a saccharide bound via an O- glycosidic bond to a hydroxyl group of the toxic payload molecule is further disclosed.

  本文披露了一种分子，其中包括一种糖苷通过O-糖苷键与毒性荷载分子的羟基结合。还披露了一种抗体药物结合物，包括一种抗体与一种毒性荷载分子共价结合，可选地通过连接基团，以及一种糖苷通过O-糖苷键与毒性荷载分子的羟基结合。
• SUGAR CHAIN CONTAINING 4-POSITION HALOGENATED GALACTOSE AND APPLICATION THEREOF
  申请人：Nishimura Shin-Ichiro

  公开号：US20090018327A1

  公开（公告）日：2009-01-15

  The present invention is directed to, for example, an oligosaccharide having at an end thereof a 4-position halogenated galactose residue represented by formula (I): (wherein X represents a halogen atom, and R represents a monosaccharide, an oligosaccharide, or a carrier), a transferase inhibitor containing the oligosaccharide, and a method for inhibiting sugar chain elongation reaction in the presence of glycosyltransferase, the method including employing the inhibitor. The invention also provides a method for producing a 4-position halogenated galactose sugar nucleotide represented by formula (II): (wherein each of R 1 to R 3 represents a hydroxyl group, an acetyl group, a halogen atom, or a hydrogen atom; X represents a halogen atom; and M represents a hydrogen ion or a metal ion), wherein the method employs bacterium-derived galactokinase and bacterium-derived hexose-1-phosphate uridylyltransferase. The invention is also directed to a sugar chain containing 4-position halogenated galactose envisaged to be employed as drugs and other materials, and to applications of the compound.

  本发明涉及一种寡糖，其末端具有由公式(I)表示的4位卤代半乳糖残基：（其中X代表卤素原子，R代表单糖，寡糖或载体），含有该寡糖的转移酶抑制剂，以及在存在糖基转移酶时抑制糖链延长反应的方法，该方法包括使用该抑制剂。该发明还提供了一种生产由公式(II)表示的4位卤代半乳糖核苷酸的方法：（其中R1至R3中的每一个代表羟基、乙酰基、卤素原子或氢原子；X代表卤素原子；M代表氢离子或金属离子），该方法利用细菌来源的半乳糖激酶和细菌来源的己糖-1-磷酸尿苷转移酶。本发明还涉及一种含有4位卤代半乳糖的糖链，可用作药物和其他材料，并涉及该化合物的应用。
• NOVEL CARBOHYDRATE FROM HUMAN CELLS AND METHODS FOR ANALYSIS AND MODIFICATION THEREOF
  申请人：Laine Jarmo

  公开号：US20100028913A1

  公开（公告）日：2010-02-04

  The invention describes reagents and methods for specific binders to glycan structures of stem cells. Furthermore the invention is directed to screening of additional binding reagents against specific glycan epitopes on the surfaces of the stem cells. The preferred binders of the glycans structures includes proteins such as enzymes, lectins and antibodies.

  该发明描述了用于特定结合干细胞糖基结构的试剂和方法。此外，该发明还涉及筛选其他结合试剂，以针对干细胞表面上的特定糖基表位。优选的糖基结构结合物包括蛋白质，如酶，凝集素和抗体。
• 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。
• Process for the preparation of O-acetyl sialic acid specific immunoglobulin and method of quantification thereof
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1083181A1

  公开（公告）日：2001-03-14

  A process for preparing O-acetyl sialic acid specific immunoglobulin comprises: (i) separating serum from blood collected from patients with acute lymphoblastic leukemia; (ii) removing low molecular weight fractions and galactose binding proteins from the serum by affinity chromatography; (iii) passing the unbound galactose free protein fraction obtained in step (ii) over a different affinity matrix from that used in step (ii) to capture the O-acetyl sialic acid specific protein fraction; (iv) eluting the specific protein fraction with a buffer at alkaline pH followed by immediate neutralization of the fraction; and (v) purifying O-acetyl sialic acid specific immunogloulin protein from the fraction obtained in step (iv). A method of quantifying the amount of O-acetyl sialic acid specific immunoglobulin protein in the serum of patients suffering from acute lymphoblastic leukemia is also disclosed and comprises the claimed process in combination with an immuno detection assay.

  一种制备 O-乙酰基丝氨酰特异性免疫球蛋白的工艺包括 (i) 从急性淋巴细胞白血病患者的血液中分离血清； (ii) 通过亲和层析从血清中去除低分子量组分和半乳糖结合蛋白； (iii) 将步骤(ii)中获得的未结合半乳糖的游离蛋白部分通过与步骤(ii)中使用的亲和基质不同的亲和基质，以捕获 O-乙酰基半乳糖特异性蛋白部分； (iv) 用碱性 pH 缓冲液洗脱特异性蛋白质部分，然后立即中和该部分；以及 (v) 从步骤(iv)中获得的馏分中纯化 O-乙酰基ialic acid 特异性免疫葡聚糖蛋白。 此外，还公开了一种量化急性淋巴细胞白血病患者血清中 O-乙酰基sialic酸特异性免疫球蛋白量的方法，该方法包括所要求的过程与免疫检测法相结合。