O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-mannopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-mannopyranose
• 英文别名: 4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-mannopyranose；GlcNAcβ(1->4)ManNAc；GlcNAc(b1-4)ManNAc；N-[(3S,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₆H₂₈N₂O₁₁
• 分子量: 424.405
• InChiKey: CDOJPCSDOXYJJF-SJQMKGADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-mannopyranose 在 citrate-phosphate buffer 、 β-N-acetylhexosaminidase from jack beans 作用下， 反应 3.0h， 生成 N-acetyl-D-mannosamine 、 D-GlcNAc
  参考文献：
  名称：

  使用β- N-乙酰己糖胺酶对2-乙酰氨基-2-脱氧-D-甘露吡喃糖二糖的酶鉴别

  摘要：

  摘要：米曲霉中的β- N-乙酰己糖胺酶选择性地区分了二糖GlcNAcβ（14）GlcNAc（1）和GlcNAcβ（14）ManNAc（2）的混合物。N，N'-二乙酰基壳二糖（1）被β- N-乙酰基己糖胺酶选择性水解，而其C-2差向异构体（2）则完全抵抗酶水解。用GalNAcβ（14）GlcNAc（3）和GalNAcβ（14）ManNAc（4）也观察到类似的区分。土曲霉，黄曲霉的β- N-乙酰己糖胺酶，牛肾和牛附睾显示出相同的选择性，而来自大豆酱油杆菌，番茄酱油杆菌，巴西青霉，草酸假单胞菌，P。funiculosum，多色的P.，Talaromyces flavus和杰克豆的酶水解了两种类型的双糖。米曲霉CCF 1066的β- N-乙酰基己糖胺酶的分子模型以及两种类型的双糖的对接实验表明，ManNAc残基导致双糖分子变形，从而导致与Trp 482发生空间冲突，从而导致恶唑啉鎓过渡态的稳定性降低通过扩展活动站点中Asp

  DOI：

  10.1002/adsc.200303002
• 作为产物：
  描述：

  N,N'-Diacetylchitobiose 在 calcium hydroxide 、 β-N-acetylhexosaminidase from Aspergillus oryzae 、 citrate phosphate buffer 作用下， 反应 2.0h， 以18%的产率得到O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-mannopyranose
  参考文献：
  名称：

  使用β- N-乙酰己糖胺酶对2-乙酰氨基-2-脱氧-D-甘露吡喃糖二糖的酶鉴别

  摘要：

  摘要：米曲霉中的β- N-乙酰己糖胺酶选择性地区分了二糖GlcNAcβ（14）GlcNAc（1）和GlcNAcβ（14）ManNAc（2）的混合物。N，N'-二乙酰基壳二糖（1）被β- N-乙酰基己糖胺酶选择性水解，而其C-2差向异构体（2）则完全抵抗酶水解。用GalNAcβ（14）GlcNAc（3）和GalNAcβ（14）ManNAc（4）也观察到类似的区分。土曲霉，黄曲霉的β- N-乙酰己糖胺酶，牛肾和牛附睾显示出相同的选择性，而来自大豆酱油杆菌，番茄酱油杆菌，巴西青霉，草酸假单胞菌，P。funiculosum，多色的P.，Talaromyces flavus和杰克豆的酶水解了两种类型的双糖。米曲霉CCF 1066的β- N-乙酰基己糖胺酶的分子模型以及两种类型的双糖的对接实验表明，ManNAc残基导致双糖分子变形，从而导致与Trp 482发生空间冲突，从而导致恶唑啉鎓过渡态的稳定性降低通过扩展活动站点中Asp

  DOI：

  10.1002/adsc.200303002

文献信息

• Enzymatic synthesis of complex glycosaminotrioses and study of their molecular recognition by hevein domains
  作者：Nuria Aboitiz、F. Javier Cañada、Lucie Hušáková、Marek Kuzma、Vladimír Křen、Jesús Jiménez-Barbero

  DOI：10.1039/b401037j

  日期：——

  Hevein, a protein found in Hevea brasiliensis, has a CRD domain, which is known to bind chitin and GlcNAc-containing oligosaccharides. By using NMR and molecular modeling as major tools we have demonstrated that trisaccharides containing GalNAc and ManNAc residues are also recognized by hevein domains. Thus far unknown trisaccharides GlcNAcβ(1→4)GlcNAcβ(1→4)ManNAc (1) and GalNAcβ(1→4)GlcNAcβ(1→4)ManNAc (2) were synthesized with the use of β-N-acetylhexosaminidase from Aspergillus oryzae. This method is based on the rather unique phenomenon that some fungal β-N-acetylhexosaminidases cannot hydrolyze disaccharide GlcNAcβ(1→4)ManNAc (5) contrary to chitobiose GlcNAcβ(1→4)GlcNAc (4) that is cleaved and, therefore, cannot be used as an acceptor for further transglycosylation. Both trisaccharides 1 and 2 were prepared by transglycosylation from disaccharidic acceptor 5 in good yields ranging from 35% to 40%. Our observations strongly indicate that the present nature of the modifications of chitotriose (GlcNAcβ(1→4)GlcNAcβ(1→4)GlcNAc, 3) at either the non-reducing end (GalNAc instead of GlcNAc) or at the reducing end (ManNAc instead of GlcNAc) do not modify the mode of binding of the trisaccharide to hevein. The association constant values indicate that chitotriose (3) binding is better than that of 1 and 2, and that the binding of 1 (with ManNAc at the reducing end) is favored with respect to that of 2 (with ManNAc at the reducing end with a non-reducing GalNAc moiety).

  Hevein是一种发现于巴西橡胶树（Hevea brasiliensis）中的蛋白质，具有CRD结构域，该结构域已知可以结合壳聚糖和含有GlcNAc的寡糖。通过利用NMR和分子建模作为主要工具，我们证明了含有GalNAc和ManNAc残基的三糖也被hevein结构域识别。目前已合成尚不为人知的三糖GlcNAcβ(1→4)GlcNAcβ(1→4)ManNAc（1）和GalNAcβ(1→4)GlcNAcβ(1→4)ManNAc（2），使用了来自枯草芽孢杆菌（Aspergillus oryzae）的β-N-乙酰氨基己糖苷酶。该方法基于一种相对独特的现象，即某些真菌β-N-乙酰氨基己糖苷酶无法水解二糖GlcNAcβ(1→4)ManNAc（5），而与其相反的壳二糖GlcNAcβ(1→4)GlcNAc（4）则会被切割，因此无法用作进一步转糖苷化的受体。两种三糖1和2均通过从二糖受体5进行转糖苷化而获得，产率较好，范围在35%至40%之间。我们的观察强烈表明，壳三糖（GlcNAcβ(1→4)GlcNAcβ(1→4)GlcNAc，3）在非还原末端（用GalNAc替代GlcNAc）或还原末端（用ManNAc替代GlcNAc）的修饰，均不改变三糖与hevein的结合方式。结合常数值表明，壳三糖（3）的结合优于1和2，而1（在还原末端为ManNAc）相较于2（在还原末端为ManNAc且非还原末端有GalNAc部分）的结合更具优势。
• Preparation of Mannac Containing Chitooligomers By Isomerisation and their Binding to Nkr-P1 Protein
  作者：Petr Sedmera、Věra Přikrylová、Karel Bezouška、Eva Rajnochová、Joachim Thiem、Vladimír Křen

  DOI：10.1080/07328309808002358

  日期：1998.12

  4-O-(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)-2-acetamido-2-deoxy-D-mannopyranose (2) was prepared from diacetylchitobiose (1) by Lobry de Bruyn-Alberda van Ekenstein rearrangement under catalysis of Ca(OH)2. The disaccharide 2 shows about ten times higher affinity than 1 towards NKR-P1 protein acting as a crucial activating receptor of rat natural killer cells (leukocytes). Chitotriose (3) can be epimerized analogously to give GlcNAc beta 1-4GlcNAc beta 1-4ManNAc (4) and its binding properties to NKR-P1 are also about ten times higher than those of 3.