低聚甘露糖醇 | 15548-39-7

• 物质功能分类: 催化剂及助剂 - 聚合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 低聚甘露糖醇
• 中文别名: 2-O-(Α-D-吡喃甘露糖基)-D-吡喃甘露糖
• 英文名称: α-D-mannopyranosyl-(1->2)-D-mannopyranoside
• 英文别名: α-D-Man-(1->2)-D-Man；2α-mannobiose；2-O-alpha-D-Mannopyranosyl-D-mannopyranose；(3S,4S,5S,6R)-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,4,5-triol
• CAS: 15548-39-7
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: HIWPGCMGAMJNRG-VXSGSMIHSA-N

物化性质

• 沸点：
  700.9±60.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  低聚甘露糖醇 在 pyridine-SO3 complex 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 [(2R,3R,4R,5S)-4,6-disulfooxy-2-(sulfooxymethyl)-5-[(2R,3S,4S,5R,6R)-3,4,5-trisulfooxy-6-(sulfooxymethyl)oxan-2-yl]oxyoxan-3-yl] hydrogen sulfate
  参考文献：
  名称：

  Probing the Interactions of Phosphosulfomannans with Angiogenic Growth Factors by Surface Plasmon Resonance

  摘要：

  The binding interactions of the phosphosulfomannan anticancer agent PI-88 (1) with the angiogenic growth factors FGF-1, FGF-2, and VEGF were studied by surface plasmon resonance (SPR) on a BIAcore 3000 biosensor. Compared with heparin, PI-88 has at least 11-fold higher affinity for FGF-1 and at least Mold higher affinity for VEGF, but at least 13-fold lower affinity for FGF-2. To define the structural features of PI-88 that are important for growth factor binding, several analogues, such as dephosphorylated PI-88 and a sulfated pentasaccharide, were prepared. The binding interactions of these analogues with FGF-1, FGF-2, and VEGF were similarly studied by SPR, and structure-activity relationships were determined.

  DOI：

  10.1021/jm030180y
• 作为产物：
  描述：

  benzyl 3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以88%的产率得到低聚甘露糖醇
  参考文献：
  名称：

  Multivalent glyconanoparticles with enhanced affinity to the anti-viral lectin Cyanovirin-N

  摘要：

  将低甘露糖（LM）结构与金纳米粒子（Au NPs）耦合，以放大 LM 与 Cyanovirin-N (CV-N) 凝集素的亲和力，并研究 CV-N 变体 CVNQ50C 和 CVNMutDB 的结构。

  DOI：

  10.1039/c1cc12981c

文献信息

• Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
  作者：Elizaveta A. Savicheva、Guyzel Yu. Mitronova、Laura Thomas、Marvin J. Böhm、Jan Seikowski、Vladimir N. Belov、Stefan W. Hell

  DOI：10.1002/anie.201908063

  日期：2020.3.27

  O-phosphorylated, and applied for reductive amination of oligosaccharides. The dyes (ϵ≈20 000 m-1  cm-1 ) with six negative charges (pH≥8) and low m/z ratios enable labeling and fluorescence detection of reducing sugars (glycans) related to the most structurally and functionally diverse class of natural products. Under excitation with a 488 nm laser, the new glycoconjugates emit yellow light of about 560 nm,

  制备在3、6和8位具有三个ω-羟基化的N-烷基磺酰胺基或烷基磺酰基残基的1-氨基py烯，进行O-磷酸化，并用于寡糖的还原胺化。具有六个负电荷（pH≥8）和低m / z比的染料（ϵ≈20 000 m-1 cm-1）能够标记和荧光检测与结构和功能最多样化的还原糖有关的还原糖（聚糖）天然产物。在488 nm激光激发下，新的糖结合物发出约560 nm的黄光，性能优于（相对于亮度和更快的电泳迁移率）相应的APTS衍生物（结合物中绿色发射的基准染料）。
• One-pot synthesis of multivalent arrays of mannose mono- and disaccharides
  作者：Wayne Hayes、Helen M.I. Osborn、Sadie D. Osborne、Robert A. Rastall、Barbara Romagnoli

  DOI：10.1016/s0040-4039(02)01855-5

  日期：2002.10

  The one-pot synthesis of multivalent arrays of mannose mono- and disaccharides, of potential use as anti-infective agents against enterobacteria infections, is described.

  描述了一锅合成的多价甘露糖单糖和二糖阵列，其潜在用途可作为抗肠道细菌感染的抗感染剂。
• Enzymatic synthesis of mannobioses and mannotrioses by reverse hydrolysis using α-mannosidase from Aspergillus niger
  作者：Katsumi Ajisaka、Ichiro Matsuo、Megumi Isomura、Hiroshi Fujimoto、Mayumi Shirakabe、Mitsuyo Okawa

  DOI：10.1016/0008-6215(95)00015-l

  日期：1995.4

  including alpha-D-man-(1 --> 2)-D man and alpha-D-man-(1 --> 2)-alpha-D-man-(1 --> 2)-D-man were formed when a highly concentrated mannose solution was incubated in the presence of alpha-mannosidase from Aspergillus niger. alpha-D-Man-(1 --> 2)-D-man and alpha-D- man-(1 --> 2)-alpha-D-man-(1 --> 2)-D-man were isolated by activated carbon chromatography followed by high performance liquid chromatography

  各种甘露寡糖，包括alpha-D-man-（1-> 2）-D man和alpha-D-man-（1-> 2）-alpha-D-man-（1-> 2）-当在来自黑曲霉的α-甘露糖苷酶存在下孵育高度浓缩的甘露糖溶液时，形成D-man。alpha-D-Man-（1-> 2）-D-man和alpha-D-Man-（1-> 2）-alpha-D-man-（1-> 2）-D-man是通过活性炭色谱分离，然后使用氨基硅胶柱进行高效液相色谱分离。除上述寡糖外，α-D-人-（1-> 3）-D-人，α-D-人-（1-> 6）-D-人和α-D-人- （1-> 2）-alpha-D-man-（1-> 6）-D-man也被分离出来。
• <i>N</i> ‐Carboxyanhydride Polymerization of Glycopolypeptides That Activate Antigen‐Presenting Cells through Dectin‐1 and Dectin‐2
  作者：Matthew N. Zhou、Corleone S. Delaveris、Jessica R. Kramer、Justin A. Kenkel、Edgar G. Engleman、Carolyn R. Bertozzi

  DOI：10.1002/anie.201713075

  日期：2018.3.12

  and synthesized the first chemically defined ligands for dectin-1 and dectin-2. They comprised glycopolypeptides bearing mono-, di-, and trisaccharides and were built through polymerization of glycosylated N-carboxyanhydrides. Through this approach, we achieved glycopolypeptides with high molecular weights and low dispersities. We identified structures that elicit a pro-inflammatory response through

  C 型凝集素 dectin-1 和 dectin-2 通过识别它们的外来聚糖结构，有助于针对微生物病原体的先天免疫。这些受体是疫苗开发和癌症免疫治疗的有希望的靶标。然而，目前可用的激动剂是来自天然来源的异质糖缀合物和多糖。在这里，我们设计并合成了第一个化学定义的 dectin-1 和 dectin-2 配体。它们包含带有单糖、二糖和三糖的糖多肽，并通过糖基化的 N-羧酸酐的聚合而构建。通过这种方法，我们获得了高分子量和低分散性的糖多肽。我们确定了通过抗原呈递细胞中的 dectin-1 或 dectin-2 引发促炎反应的结构。
• Preferential binding of <i>E. coli</i> with type 1 fimbria to <scp>d-</scp>mannobiose with the Manα1→2Man structure
  作者：Katsumi Ajisaka、Kaoru Yuki、Kaori Sato、Nozomi Ishii、Ichiro Matsuo、Ryo Kuji、Tatsuo Miyazaki、Kiyoshi Furukawa

  DOI：10.1080/09168451.2015.1075863

  日期：2016.1.2

  Manα1→2Man, Manα1→3Man, Manα1→4Man, and Manα1→6Man were converted to the glycosylamine derivatives. Then, they were mixed with monobenzyl succinic acid to obtain their amide derivatives. After removing the benzyl group by hydrogenation, the succinylamide derivatives were coupled with the hydrazino groups on BlotGlyco™ beads in the presence of water-soluble carbodiimide. d-Mannobiose-linked beads were incubated with fluorescence-labeled Escherichia coli with type 1 fimbria, and the number of the fluorescent dots associated with the beads was counted in order to determine the binding preference among d-mannobiose isomers. The results showed that the bacteria bind strongly to Manα1→2Man1→beads, Manα1→3Man1→beads, Manα1→4Man1→beads, and Manα1→6Man1→beads, in order. In the presence of 0.1 M methyl α-d-mannopyranoside, most of the bacteria failed to bind to these beads. These results indicate that E. coli with type 1 fimbria binds to all types of d-mannobiose isomers but preferentially to Manα1→2Man disaccharide.

  摘要：Manα1→2Man、Manα1→3Man、Manα1→4Man和Manα1→6Man被转化为糖胺衍生物。然后，它们与单苯甲酰琥珀酸混合以获得酰胺衍生物。在氢化去除苄基后，琥珀酰胺衍生物在水溶性碳二亚胺存在下与BlotGlyco™珠上的肼基结合。d-甘露二糖连接的珠子与带有1型纤毛的荧光标记大肠杆菌孵育，然后计算与珠子相关的荧光点的数量，以确定对d-甘露二糖异构体的结合偏好。结果显示，细菌强烈结合到Manα1→2Man1→珠子、Manα1→3Man1→珠子、Manα1→4Man1→珠子和Manα1→6Man1→珠子，依次顺序。在存在0.1 M甲基α-d-甘露聚糖时，大多数细菌未能结合到这些珠子。这些结果表明，带有1型纤毛的大肠杆菌结合所有类型的d-甘露二糖异构体，但优先结合到Manα1→2Man二糖。