N-acetylallolactosamine | 183811-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetylallolactosamine
• 英文别名: β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranose；2-acetamido-2-deoxy-6-O-β-galactopyranosyl-D-glucose；allo-N-acetyllactosamine；allo-LacNAc；Gal-β-(1->6)-GlcNAc；Galβ1-6GlcNAc；Gal(b1-6)b-GlcNAc；N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]acetamide
• CAS: 183811-88-3
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: ACKXCNXSQYSCQN-RIZIMNAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 β-glucosidase from Bifidobacterium bifidum 氢氟酸 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 乙二醇乙醚 、 phosphate buffer 为溶剂， 反应 10.0h， 生成 N-acetylallolactosamine
  参考文献：
  名称：

  The efficient enzymatic synthesis of N-acetyllactosamine in an organic co-solvent

  摘要：

  In the presence of beta-galactosidase from Bifidobacterium bifidum, N-acetyllactosamine was synthesized in significantly enhanced yield compared with earlier routes. Different proportions of the (1-->4)- and (1-->6)-linked forms were obtained depending on the choice of enzyme and reaction conditions, viz. the nature of added organic co-solvent (20-80% of 2-ethoxy ethyl ether, trimethyl phosphate, or acetone). The beta-(1 --> 4)-linked disaccharide was the major product and the beta-(1-->6)-linked disaccharide was the minor product. With beta-galactosidases from P. multicolor, A. oryzae, B. longum the beta-(1 --> 6) linkage was exclusively synthesized. Procedures for optimising the yield of N-acetyllactosamine are discussed. An immobilized enzyme on a nylon powder column was used for the efficient recycling of enzyme and synthesizing the disaccharide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00063-x

文献信息

• Solvents derived from glycerol modify classical regioselectivity in the enzymatic synthesis of disaccharides with Biolacta β-galactosidase
  作者：María Pérez-Sánchez、Manuel Sandoval、Alvaro Cortés-Cabrera、Héctor García-Marín、José V. Sinisterra、José I. García、María J. Hernaiz

  DOI：10.1039/c1gc15266a

  日期：——

  Green solvents made from glycerol change the classical regioselectivity of Biolacta No 5 β-galactosidase, from β(1→4) to β(1→6) linkages when a 2 M concentration was used. In order to explain these results, the non-proteic compounds present in the Biolacta preparation were separated by precipitation with ammonium sulfate and the remaining protein extract was used to set reactions with appropriate organic

  绿色的 溶剂 由...制成 甘油当使用2 M浓度时，将Biolacta N o 5β-半乳糖苷酶的经典区域选择性从β（1→4）变为β（1→6）键。为了解释这些结果，Biolacta制剂中存在的非蛋白质化合物通过沉淀 和 硫酸铵 其余的 蛋白质 提取物用于设定与适当有机物的反应 溶剂发现保留了对β（1→6）异构体的区域选择性。根据蛋白质组学分析，发现肺炎链球菌与Biolactaβ-半乳糖苷酶制剂之间有98％的同源性。利用这些数据，完成了分子建模，预测了三维空间中的三维相互作用。酵素 与捐赠者一起活动的地点（GlcNAc）和 水--溶剂 解释这种现象的混合物。
• Sustainable synthesis of N-acetyllactosamine using an immobilized β-galactosidase on a tailor made porous polymer
  作者：Antonio Aires-Trapote、Aitana Tamayo、Juan Rubio、Angel Rumbero、María J. Hernáiz

  DOI：10.1039/c5ra03527a

  日期：——

  Porous polymer particles containing surface epoxy groups were synthesized for immobilizing β-galactosidase from Bacillus circulans. Enzyme immobilization was achieved by covalent attachment to a custom made porous polymer and the biocatalyst was characterized in terms of optimal pH and thermal stability, and its catalytic efficiency evaluated for synthesizing N-acetyllactosamine (Gal-β-(1 → 4)-GlcNAc)

  合成了具有表面环氧基团的多孔聚合物颗粒，用于固定来自环状芽孢杆菌的β-半乳糖苷酶。通过共价连接到定制的多孔聚合物上实现酶的固定化，并根据最佳pH和热稳定性对生物催化剂进行了表征，并评估了其催化合成N-乙酰基乳糖胺（Gal-β-（1→4）-GlcNAc）的催化效率。在不同溶剂中，并用1：5的摩尔供体的（比p受体糖胺（GlcNAc）：NP-β-GAL）。反应以高转化率和区域选择性进行。使用生物溶剂3可获得高达60％的β-（1→4）被发现。在相同的反应条件下进行可重复使用性分析，发现固定的酶在20批反应后保留了约85％的活性，转化率超过60％。此外，实现了反应放大，生物溶剂回收和再循环，并保持了催化活性。
• Glycosyl Azides – An Alternative Way to Disaccharides
  作者：Pavla Bojarová、Lucie Petrásková、Erica Elisa Ferrandi、Daniela Monti、Helena Pelantová、Marek Kuzma、Pavla Simerská、Vladimír Křen

  DOI：10.1002/adsc.200700028

  日期：2007.6.4

  good yields. The versatility of glycosyl azides was demonstrated in the synthesis of five disaccharides – two of them are described for the first time. All the reactions were highly regioselective, yielding β(16) isomers. β-Galactosidase from E. coli proved to have the best synthetic capabilities. The present study shows that glycosyl azides are a valuable alternative to common p-nitrophenyl glycoside

  糖基叠氮化物显示为β-半乳糖苷酶，β-葡萄糖苷酶和α-甘露糖苷酶的有效供体。仅α-半乳糖苷酶不能裂解各自的叠氮糖苷1，而且它们表现出竞争性抑制作用（尤其是来自黄萎病菌（Talaromyces flavus）的α-半乳糖苷酶）。高水溶性和糖基叠氮化物的现成合成即使具有困难的受体如N-乙酰基-D-甘露糖胺也能以高收率进行转糖基化反应。五个双糖的合成证明了糖基叠氮化物的多功能性–首次描述了其中的两个。所有反应都是高度区域选择性的，产生β（16）异构体。大肠杆菌的β-半乳糖苷酶被证明具有最佳的合成能力。本研究表明，在许多合成反应中，糖基叠氮化物是常见的对硝基苯基糖苷供体的一种有价值的替代物。
• Improved synthesis of disaccharides with Escherichia coli β-galactosidase using bio-solvents derived from glycerol
  作者：María Pérez-Sánchez、Álvaro Cortés Cabrera、Héctor García-Martín、J. Vicent Sinisterra、José I. García、María J. Hernáiz

  DOI：10.1016/j.tet.2011.08.009

  日期：2011.10

  A noticeably increase in activity, keeping total regioselectivity was found in the synthetic behaviour of Escherichia coli beta-galactosidase in glycerol-based solvents using a 1:7 molar ratio of donor (pNP-beta-Gal): acceptor (GlcNAc). Yields of up to 97% of beta(1 -> 6) with different solvents were found. These reactions take place without noticeable hydrolytic activity and with total regioselectivity, representing a considerable improvement over the use of aqueous buffer or conventional organic solvents. There is a clear dependence of the catalytic results on the solvent structure, which is analysed in terms of polarity and hydrophobicity. (C) 2011 Published by Elsevier Ltd.
• One-pot synthesis of β-d-Gal>(1 → 4)[β-d-Galp(1 → 6)]-d-GlcNAc, a ‘core’ trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi
  作者：Carola Gallo-Rodriguez、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1016/s0008-6215(97)00256-5

  日期：1997.12

  Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (4) with penta-O-benzoyl-beta-D-galactopyranose (6) gave the derivative of beta-D-Galp-(1 --> 6)-alpha-D-GlcNAc 7 in 80% yield, This was glycosylated with penta-O-benzoyl-alpha,beta- D-galactofuranose (5>, employing the same catalyst, to afford the protected benzyl per-O-benzoyl-beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]D-GlcNAc 10 in 41% yield, Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). beta-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi. (C) 1998 Elsevier Science Ltd.