α-D-mannopyranosyl-(1->6)-α,β-D-mannose | 15548-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-mannopyranosyl-(1->6)-α,β-D-mannose
• 英文别名: α-D-mannopyranosyl-(1->6)-D-mannopyranoside；α-D-mannopyranosyl-(1->6)-D-mannopyranose；α-D-man-(1<*>6)-D-man；mannosyl-α(1->6)-mannose；α-D-Man-(1->6)-D-Man；α-1,6-mannobiose；6-O-alpha-D-Mannopyranosyl-D-mannopyranose；(3S,4S,5S,6R)-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 15548-40-0
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DLRVVLDZNNYCBX-FZFXURTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 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

反应信息

• 作为反应物：
  描述：

  α-D-mannopyranosyl-(1->6)-α,β-D-mannose 在 α-D-mannosidase from the seeds of Kaya 、 Torreya nucifera 作用下， 以 水 为溶剂， 生成 甘露糖
  参考文献：
  名称：

  Purification and Characterization ofα-D-Mannosidase from the Seeds ofKaya, Torreya nucifera

  摘要：

  从香榧种子提取物中纯化出了α-D-甘露糖苷酶。纯化后的酶的分子质量为 3.6 × 105 道尔顿。这种酶的最适 pH 值为 4.5，在 pH 值为 5.5 和 6.5 之间稳定。该酶似乎是一种含 Zn2+ 的金属酶。该酶可水解对硝基苯-α-D-甘露糖苷、甲基-α-D-甘露糖苷、α-1-"3-甘露寡糖和α-1-"6-甘露寡糖，其 Km 值分别为 0.785 mM、0.236 M、2.505 mM 和 0.268 mM。对各种z-连接甘露寡糖的水解表明，该酶水解α-甘露寡糖的顺序为α-（1→2）>-（1→6）>-（1→3）。

  DOI：

  10.1271/bbb.60.687
• 作为产物：
  描述：

  甘露糖 在 sodium acetate buffer 、 transglucosidase L from Amano 作用下， 反应 408.0h， 以1.76 g的产率得到α-D-mannopyranosyl-(1->6)-α,β-D-mannose
  参考文献：
  名称：

  Glycosidase-catalysed synthesis of mannobioses by the reverse hydrolysis activity of α-mannosidase: partial purification of α-mannosidases from almond meal, limpets and Aspergillus niger

  摘要：

  Two disaccharides, alpha-D-Manp-(1-->2)-D-Manp 6 and alpha-D-Manp-(1-->3)-D-Manp 7, were synthesised from mannose using the reverse hydrolysis activity of the partially purified alpha-mannosidases from almond (Prunus amygdalus) meal and limpets (Patella vulgata). Both disaccharides were isolated by carbon-Celite chromatography. Attempts were also made towards the synthesis of core pentasaccharide using the purified alpha-mannosidase from Aspergillus niger. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00532-7

文献信息

• 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。
• 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。
• Enzymatic synthesis of unique sialyloligosaccharides using marine bacterial α-(2→3)- and α-(2→6)-sialyltransferases
  作者：Toshiki Mine、Tatsuo Miyazaki、Hitomi Kajiwara、Kenta Naito、Katsumi Ajisaka、Takeshi Yamamoto

  DOI：10.1016/j.carres.2010.03.036

  日期：2010.7

  products, we confirmed their structure by NMR spectroscopy. The alpha-(2-->3)-sialyltransferase transferred N-acetylneuraminic acid (Neu5Ac) from cytidine 5'-monophospho-N-acetylneuraminic acid (CMP-Neu5Ac) to the beta-anomeric hydroxyl groups of mannose (Man) and alpha-Manp-(1-->6)-Manp, and alpha-(2-->6)-sialyltransferase transferred N-acetylneuraminic acid to the 6-OH groups of the non-reducing end

  我们调查了克隆自Photobacter sp。的海洋细菌α-（2-> 3）-唾液酸转移酶的受体底物特异性。使用几种糖类作为受体底物，从达姆酵母菌JT0160克隆的JT-ISH-224和α-（2-> 6）-唾液酸转移酶。纯化酶促反应产物后，我们通过NMR光谱确认了其结构。α-（2-> 3）-唾液酸转移酶将N-乙酰神经氨酸（Neu5Ac）从胞苷5'-单磷酸-N-乙酰神经氨酸（CMP-Neu5Ac）转移至甘露糖（Man）和α的β-异头羟基-Manp-（1-> 6）-Manp和α-（2-> 6）-唾液酸转移酶将N-乙酰神经氨酸转移至β-Galp-（ 1-> 3）-GlcpNAc和beta-Galp-（1-> 6）-GlcpNAc。
• Disaccharides as Sialic Acid Aldolase Substrates: Synthesis of Disaccharides Containing a Sialic Acid at the Reducing End
  作者：Shengshu Huang、Hai Yu、Xi Chen

  DOI：10.1002/anie.200604799

  日期：2007.3.19
• A novel two-step synthesis of α-linked mannobioses based on an acid-assisted reverse hydrolysis reaction
  作者：Katsumi Ajisaka、Misato Yagura、Tatsuo Miyazaki

  DOI：10.1016/j.carres.2011.10.037

  日期：2012.1

  Instead of an enzyme-assisted reverse hydrolysis reaction for the synthesis of manno-oligosaccharides, we propose here a versatile new approach. By Fischer type glycosylation, a D-mannose solution of extremely high concentration (approximately 83% (w/w)) was incubated at 60 degrees C for 65 h in 0.5 M HCl. After dilution and neutralization, the small amount of formed beta-linked oligosaccharides was hydrolyzed by beta-mannosidase. The yields of alpha-D-Manp-(1 -> 2)-D-Manp (7.9%), alpha-D-Manp-(1 -> 3)-D-Manp (7.9%), and alpha-D-Manp-(1 -> 6)-D-Manp (29.1%) isolated by an activated carbon column chromatography were almost identical to those of the enzymatic reaction, but the yield of alpha-D-Manp-(1 -> 3)-D-Manp increased enormously by the present method. (C) 2011 Elsevier Ltd. All rights reserved.