2-(ALPHA-D-甘露糖基硫基)亚氨基乙酸甲酯 | 61145-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(ALPHA-D-甘露糖基硫基)亚氨基乙酸甲酯
• 英文名称: 2-imino-2-methoxyethyl 1-thio-α-D-mannopyranoside
• 英文别名: 2-imino-2-methoxyethyl-1-thiomannoside；2-imino-2-methoxyethyl 1-thio-alpha-D-mannopyranoside；methyl 2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethanimidate
• CAS: 61145-44-6
• 化学式: C₉H₁₇NO₆S
• 分子量: 267.303
• InChiKey: QMZQMASPATYOGL-RZNRLUQXSA-N

物化性质

• 沸点：
  460.2±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (pal)₂KRSSSGSGSGSGSGK-NH₂ 、 2-(ALPHA-D-甘露糖基硫基)亚氨基乙酸甲酯 在 吡啶 、 三甲胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of high functionality and quality mannose-grafted lipids to produce macrophage-targeted liposomes

  摘要：

  The mannose receptor, which is responsible for tumor invasion, proliferation, and metastasis in the tumor microenvironment, is overexpressed in tumor-associated macrophages. Mannose is commonly applied to PEGylated liposomes in macrophage-targeted cancer therapy. To develop a high functionality and quality (HFQ) lipid for macrophage-targeted liposomes, we designed a novel mannosylated lipid with improved mannose receptor binding affinity using serine-glycine repeats (SG)(n). We synthesized Man(S)-(SG)(5)-SSK-K(Pal)(2) using only a fluorenylmethyloxycarbonyl (Fmoc) protecting group solid-phase peptide synthesis method, which produced a high-quality lipid at a moderately good yield. We then prepared Man-(SG)(5)/PEGylated liposomes using a post-insertion technique to insert Man(S)-(SG)(5)-SSK-K(Pal)(2 )into the PEGylated liposomes. In vitro cell investigations revealed that the Man-(SG)(5)/PEGylated liposomes effectively associated with mouse peritoneal macrophages by interacting with the mannose receptors. The results suggest that we produced a novel high-quality, highly functional mannosylated lipid that is suitable for clinical drug delivery applications.

  DOI：

  10.1016/j.ejps.2018.07.036
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 sodium disulfite 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 50.0h， 生成 2-(ALPHA-D-甘露糖基硫基)亚氨基乙酸甲酯
  参考文献：
  名称：

  糖病毒：化学糖基化重新靶向腺病毒基因转移。

  摘要：

  DOI：

  10.1002/anie.200461832

文献信息

• Chemoenzymatic synthesis of neoglycoproteins driven by the assessment of protein surface reactivity
  作者：T. Bavaro、M. Filice、C. Temporini、S. Tengattini、I. Serra、C. F. Morelli、G. Massolini、M. Terreni

  DOI：10.1039/c4ra11131a

  日期：——

  2-iminomethoxyethyl mannose-based mono- and disaccharides have been synthesized by a chemoenzymatic approach and used in coupling reactions with ε-amino groups of lysine residues in a model protein (ribonuclease A, RNase A) to give semisynthetic neoglycoconjugates. In order to study the influence of structure of the glycans on the conjugation outcomes, an accurate characterization of the prepared neoglycoproteins was

  本文通过化学酶法合成了一系列基于2-亚氨基甲氧基乙基甘露糖的单糖和二糖，并将其用于与模型蛋白（核糖核酸酶A，RNase A）中赖氨酸残基的ε-氨基偶联反应，得到半合成糖。新糖缀合物。为了研究聚糖结构对偶联结果的影响，通过结合ESI-MS和LC-MS分析方法对制备的新糖蛋白进行了准确表征。对所有新糖缀合物的胰凝乳蛋白酶消化物的分析显示六个Lys-糖基化位点，其赖氨酸反应性的顺序如下：Lys 1≫ Lys 91≅Lys 31> Lys 61≅Lys 66。K a，蛋白质柔韧性）。将在硅片评价似乎证实了赖氨酸的反应从蛋白质组分析产生的顺序。
• Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation
  作者：Stewart R. Alexander、Antony J. Fairbanks

  DOI：10.1039/c6ob01069e

  日期：——

  Unprotected carbohydrates can be directly converted into cyanooethyl thioglycosides, which in turn may be used for protein glycosylation, in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution.

  未保护的碳水化合物可以直接转化为氰乙基硫代糖苷，然后可以通过与2-氯-1,3-二甲基咪唑氯化铵（DMC）和硫代乙腈在水溶液中反应的方式，完全立体选择性地用于蛋白质糖基化。
• Cell-specific ligands for selective drug delivery to tissues and organs
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、James C. Robbins、T. W. Doebber、T. Y. Shen

  DOI：10.1021/jm00144a004

  日期：1981.12

  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.
• Glycoviruses: Chemical Glycosylation Retargets Adenoviral Gene Transfer
  作者：Oliver M. T. Pearce、Kerry D. Fisher、Julia Humphries、Leonard W. Seymour、Alberto Smith、Benjamin G. Davis

  DOI：10.1002/anie.200461832

  日期：2005.2.4
• Synthesis of high functionality and quality mannose-grafted lipids to produce macrophage-targeted liposomes
  作者：Masayori Hagimori、Yorinao Chinda、Tadaharu Suga、Kazuto Yamanami、Naoya Kato、Tatsuo Inamine、Yuki Fuchigami、Shigeru Kawakami

  DOI：10.1016/j.ejps.2018.07.036

  日期：2018.10

  The mannose receptor, which is responsible for tumor invasion, proliferation, and metastasis in the tumor microenvironment, is overexpressed in tumor-associated macrophages. Mannose is commonly applied to PEGylated liposomes in macrophage-targeted cancer therapy. To develop a high functionality and quality (HFQ) lipid for macrophage-targeted liposomes, we designed a novel mannosylated lipid with improved mannose receptor binding affinity using serine-glycine repeats (SG)(n). We synthesized Man(S)-(SG)(5)-SSK-K(Pal)(2) using only a fluorenylmethyloxycarbonyl (Fmoc) protecting group solid-phase peptide synthesis method, which produced a high-quality lipid at a moderately good yield. We then prepared Man-(SG)(5)/PEGylated liposomes using a post-insertion technique to insert Man(S)-(SG)(5)-SSK-K(Pal)(2 )into the PEGylated liposomes. In vitro cell investigations revealed that the Man-(SG)(5)/PEGylated liposomes effectively associated with mouse peritoneal macrophages by interacting with the mannose receptors. The results suggest that we produced a novel high-quality, highly functional mannosylated lipid that is suitable for clinical drug delivery applications.