2-carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside | 79360-22-8

• 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: 2-carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• 英文别名: S-α-3'-propionyl tetra-O-acetyl thiomannoside；2-Carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranoside；3-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpropanoic acid
• CAS: 79360-22-8
• 化学式: C₁₇H₂₄O₁₁S
• 分子量: 436.437
• InChiKey: FGMXMRUEYSIRLE-FMPTWSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 N²,N⁶-bis<3-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thio>propionyl>-D-lysine
  参考文献：
  名称：

  Cell-specific ligands for selective drug delivery to tissues and organs

  摘要：

  Various numbers of D-mannose residues have been attached via spacer arms to lysine, dilysine, and oligolysine backbones. These D-mannosyl peptide analogues were found to be potent competitive inhibitors of the uptake of 125I-labeled D-mannose-bovine serum albumin conjugate by rat alveolar macrophages. The inhibitory potency of these synthetic ligands increased with increasing number of carbohydrate moieties. The chirality of the peptide backbone did not appear to play a major role in binding, whereas variations of the length and linkage of the spacer arm notably affected the inhibitory activities. The saccharide specificity of the macrophage receptor was demonstrated by the inactivity of the corresponding D-galactosyl peptide analogues. The L-fucosyl peptide derivative was only weakly active. The trimannosyldilysine ligand (KI = 3.9 microM) and its analogues are potentially useful in selective delivery of therapeutic agents to macrophages.

  DOI：

  10.1021/jm00144a004
• 作为产物：
  描述：

  3-碘丙酸 在 硫脲 、 potassium pyrosulfite 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Methods for delivery of nucleic acids

  摘要：

  这项发明涉及用于将核酸（例如，DNA、RNA、PNA及其杂合体）递送到细胞中的方法和组合物。本发明的核酸递送复合物使得生物活性的核酸能够以某种方式和形式递送到体外和体内的细胞和生物体中，从而允许核酸执行其所需的生物学功能。

  公开号：

  US20060084617A1

文献信息

• Galenical formulations
  申请人：Platzek Johannes

  公开号：US20060093554A1

  公开（公告）日：2006-05-04

  This invention describes new galenical formulations that contain paramagnetic and diamagnetic perfluoroalkyl-containing compounds. The new formulations are suitable as contrast media for nuclear spin tomography.

  这项发明描述了包含顺磁和抗磁全氟烷基化合物的新制剂。这些新制剂适用于核磁共振断层扫描作为对比介质。
• Cell-specific glycopeptide ligands
  申请人：Merck & Co., Inc.

  公开号：US04386026A1

  公开（公告）日：1983-05-31

  Cell-specific ligands comprising conjugates of saccharides and amino acids or peptides are synthesized from amino acids such as ornithine, lysine, peptides such as dilysine, diornithine or oligolysine and selected saccharides having reactive functional groups protected by appropriate blocking groups. Such glycopeptides are useful as tissue specific substances, which when coupled with bioactive materials through metabolizable or hydrolyzable linkages, deliver such bioactive materials to the selected site. In this manner, antiinflammatory drugs such as dexamethasone are linked through a metabolizable or hydrolyzable linkage and on administration to an animal suffering from inflammatory disease carries the drug to the site of inflammation for intracellular release. Other examples include the macrophage ligand N.sup.2 -N.sup.2, N.sup.6 -Bis-[3-(.alpha.-D-mannopyranosylthio)propionyl]-6-lysyl-N.sup.6 -[3-(.alpha.-D-mannopyranosylthio)propionyl]-L-lysine, 5, which when coupled to .beta.-glucocerebrosidase, can deliver the enzyme selectively to kupffer cells. This is useful in the enzyme replacement therapy of Gaucher's disease.

  由氨基酸（如鸟氨酸，赖氨酸）、肽（如双赖氨酸、双鸟氨酸或寡赖氨酸）和选定的具有适当阻断基保护的反应性官能团的糖组成的细胞特异性配体被合成。这种糖肽可用作组织特异性物质，当通过可代谢或可水解的连接与生物活性材料耦合时，可将这些生物活性材料输送到所选的部位。通过这种方式，例如，抗炎药物如地塞米松通过可代谢或可水解的连接与之链接，并在对患有炎症性疾病的动物进行治疗时将药物带到炎症部位进行细胞内释放。其他例子包括巨噬细胞配体N.sup.2-N.sup.2，N.sup.6-Bis-[3-(.alpha.-D-mannopyranosylthio)propionyl]-6-lysyl-N.sup.6-[3-(.alpha.-D-mannopyranosylthio)propionyl]-L-lysine，5，当与β-葡聚糖酶耦合时，可以将酶有选择地输送到库普弗细胞。这在高氏病的酶替代疗法中非常有用。
• Use of perfluoroalkyl-containing metal complexes as contrast media in MR-imaging for visualization of plaque, tumors and necroses
  申请人：——

  公开号：US20030072713A1

  公开（公告）日：2003-04-17

  The invention relates to the use of perfluoroalkyl-containing metal complexes that have a critical micelle formation concentration <10 −3 mol/l, a hydrodynamic micelle diameter (2 Rh)>1 nm and a proton relaxivity in plasma (R 1 )>10 l/mmol·s) as contrast media in MR imaging for visualization of plaque, lymph nodes, infarcted and necrotic tissue and for independent visualization of necrotic tissue and tumor tissue.

  本发明涉及使用临界胶束形成浓度小于10-3mol/l，水动力学胶束直径（2Rh）大于1nm，血浆中质子弛豫时间（R1）大于10l/mmol·s的含有全氟烷基的金属配合物作为MR成像的对比介质，用于可视化斑块、淋巴结、梗死和坏死组织以及独立可视化坏死组织和肿瘤组织。
• Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers
  作者：Socorro Espuelas、Philippe Haller、Francis Schuber、Benoı̂t Frisch

  DOI：10.1016/s0960-894x(03)00472-4

  日期：2003.8

  We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of glycopeptide dendrimers, dimerization and affinity for Concanavalin A
  作者：Ronan Euzen、Jean-Louis Reymond

  DOI：10.1016/j.bmc.2011.03.047

  日期：2011.5

  We described herein the synthesis of second generation glycopeptide dendrimers G2a-g presenting variable amino acids placed internally into the multivalent scaffold. The effect of such structural modulation on recognition processes by Concanavalin A (Con A), was then estimated by enhanced-sensitivity Enzyme-Linked Lectin Assay (ELLA). In a complementary study, glycopeptide dendrons of different valencies and including a L-cysteine residue before the dendritic core (G0SH, G1SH and G2SH), were also synthesized and homodimerized. Then, the disulfide-containing glycopeptide dendrimers generated by this convergent approach (G0(2)S(2), G1(2)S(2) and G2(2)S(2)) were used as Con A inhibitors and assayed by ELLA. (C) 2011 Elsevier Ltd. All rights reserved.