6-azidohexyl-O-[2-deoxy-2-acetamido-4-O-(β-D-galactopyranosyl)]-β-D-glucopyranoside | 209671-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azidohexyl-O-[2-deoxy-2-acetamido-4-O-(β-D-galactopyranosyl)]-β-D-glucopyranoside
• 英文别名: 6-azidohexyl (β-D-galactopyranosyl)-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-2-(6-azidohexoxy)-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 209671-46-5
• 化学式: C₂₀H₃₆N₄O₁₁
• 分子量: 508.526
• InChiKey: ODUGZRIAJIWISA-KDKNCOTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  202
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-azidohexyl-O-[2-deoxy-2-acetamido-4-O-(β-D-galactopyranosyl)]-β-D-glucopyranoside 在 无机焦磷酸酶 、 glucose-1-phosphate thymidylyltransferase from Aneurinibacillus thermoaerophilus DSM₁₀₁₅₅ 、 N-acetylhexosamine kinase from Bifidobacterium longum 、 recombinant galactokinase from Meiothermustaiwanensis sp. nov. WR-220 、 recombinant PmST 、 尿苷-5'-三磷酸 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Sequential one-pot enzymatic synthesis of oligo-N-acetyllactosamine and its multi-sialylated extensions

  摘要：

  一种简单高效的方案，用于制备不同长度的寡糖-N-乙酰乳糖胺（oligo-LacNAc）及其多唾液酸化扩展物的制备规模合成协议。

  DOI：

  10.1039/c4cc01227e
• 作为产物：
  描述：

  半乳糖-1-磷酸 在 无机焦磷酸酶 、 recombinant thymidylyltransferase from Aneurinibacillus thermoaerophilus DSM 10155 、 尿苷-5'-三磷酸 、 magnesium chloride 作用下， 反应 5.0h， 生成 6-azidohexyl-O-[2-deoxy-2-acetamido-4-O-(β-D-galactopyranosyl)]-β-D-glucopyranoside
  参考文献：
  名称：

  葡萄糖-1-磷酸胸苷基转移酶在尿苷5'-二磷酸半乳糖的合成中的应用及其在N-乙酰乙酰半乳糖胺合成中的应用

  摘要：

  在这项研究中，我们描述了野生型细菌胸苷基转移酶（RmlA）直接合成尿苷5'-二磷酸半乳糖（UDP-Gal），自然界中用于合成胸苷5'-二磷酸葡萄糖（TDP-葡萄糖） 。通过使用镁（Mg 2+）作为辅助因子，反应温度为55°C，RmlA可以实现100毫克规模的UDP-Gal合成。此外，RmlA被定点和共价固定在磁性纳米颗粒（MNPa）上。在十次连续的酶法测定中重复使用后，所得RmlA-MNP复合物保留了其活性的几乎95％。此外，脑膜炎奈瑟氏球菌的β-1,4-半乳糖基转移酶（GalT）通过使用intein介导的蛋白质表达系统成功地成功表达和纯化了p53。GalT在25°C下相对稳定，并且在DTT和BSA的存在下其活性得到增强。因此，在依次添加酶和调节反应温度的情况下，使用RmlA和GalT合成N-乙酰基乳糖胺（LacNAc）是可行的。这些结果证明了细菌RmlA在碳水化合物合成中的潜在应用。

  DOI：

  10.1002/adsc.201100402

文献信息

• Synthesis and Characterization of Sulfated Gal-<i>β</i>-1,3/4-GlcNAc Disaccharides through Consecutive Protection/Glycosylation Steps
  作者：Zhijay Tu、Hsiao-Wu Hsieh、Chih-Ming Tsai、Chia-Wei Hsu、Shy-Guey Wang、Kuan-Jung Wu、Kuo-I Lin、Chun-Hung Lin

  DOI：10.1002/asia.201201204

  日期：2013.7

  3/4‐GlcNAc, which allowed for the systematic introduction of a sulfate group onto the C3/C6 positions of Gal and/or the C6 position of GlcNAc. In particular, the disaccharide precursors were prepared in five or six steps and high overall yield from para‐tolyl‐6‐O‐tert‐butyldiphenylsilyl‐1‐thio‐β‐D‐galactopyranoside. After deprotection and sulfation steps, the final products were characterized by using several

  我们已经开发了一种迅速过程，以产生大量的正交保护的GAL-的β 1,3 / 4-GlcNAc的，其允许系统地引入硫酸基的半乳糖上和/或GlcNAc的的C6位置的C3 / C6的位置。特别是，二糖前体分五步或六步制备，并从对-甲苯基-6- O-叔丁基-丁基二苯基甲硅烷基-1-硫代β - D-吡喃半乳糖苷中获得较高的总收率。经过脱保护和硫酸化步骤后，使用几种NMR方法对最终产物进行表征，以明确确定每个引入的硫酸根基团的位置，并检查它们与人半乳糖凝集素-1和半乳糖凝集素-8的结合特异性。
• Water-Soluble Sulfo-Fluorous Affinity (SOFA) Tag-Assisted Enzymatic Synthesis of Oligosaccharides
  作者：Kai-Ling Hou、Pei-Yun Chiang、Chien-Hung Lin、Ben-Yuan Li、Wei-Ting Chien、Yu-Ting Huang、Ching-Ching Yu、Chun-Cheng Lin

  DOI：10.1002/adsc.201800085

  日期：2018.6.15

  Herein, we report a bifunctional sulfo‐fluorous affinity (SOFA) tag‐assisted enzymatic synthesis and purification strategy for the facile preparation of bioactive glycans using fluorous solid‐phase extraction (FSPE). The incorporation of a sulfonate moiety onto the heavy fluorous tag significantly increases its water solubility, which allows the broad use of the inherently hydrophobic fluorous tag

  本文中，我们报告了一种双功能磺基-氟亲和力（SOFA）标签辅助的酶法合成和纯化策略，用于使用氟固相萃取（FSPE）轻松制备生物活性聚糖。将磺酸盐部分结合到重的氟标签上显着增加了其水溶性，这允许在水性缓冲液中广泛使用固有疏水性的氟标签。此外，SOFA标签还包含可光裂解的接头，可通过紫外线辐射轻松释放氨基官能化的寡糖。SOFA标签用于带负电荷的聚糖和中性聚糖的合成，以证明其广泛用作六种不同糖基转移酶的受体，从而显着提高了使用FSPE制备复杂聚糖的可行性。所有反应均在水性缓冲液中进行，使用最少量的甲醇纯化产物，光辐照后很容易回收SOFA标签。因此，整个合成过程对环境无害。
• Substrate Characterization of <i>Bacteroides fragilis</i> α1,3/4-Fucosyltransferase Enabling Access to Programmable One-Pot Enzymatic Synthesis of KH-1 Antigen
  作者：Hsin-Hui Huang、Jia-Lin Fang、Hung-Kai Wang、Chih-Yuan Sun、Teng-Wei Tsai、Yu-Ting Huang、Cheng-Yu Kuo、Yi-Jyun Wang、Chi-Chun Liao、Ching-Ching Yu

  DOI：10.1021/acscatal.9b04182

  日期：2019.12.6

  for the synthesis of various fucosides, including Lex, Ley, blood group H1-antigen, 3FL, LNFP III, LNFP V, LNnFP V, LNDFH II, LNDFH III, IFLNH III, DF-pLNnH, and TF-pLNnH, and hybrid-type glycans, such as Ley-3FL and Ley-Lex-3FL. The preferential fucosylation activity on Fucα1,2LacNAc and LacNAc over Lac, which enabled programmable fucosylation, led to the one-pot synthesis of a KH-1 antigen.

  脆弱拟杆菌（Bacteroides fragilis） α1,3/ 4-岩藻糖基转移酶（Bf13FT）在大肠杆菌中表达，并被表征为α1,3/ 4-岩藻糖基转移酶，可用作合成各种岩藻糖苷（包括Le x，Le y，血型H 1-抗原，3FL，LNFP III，LNFP V，LNnFP V，LNDFH II，LNDFH III，IFLNH III，DF- p LNnH和TF- p LNnH，以及杂合型聚糖，例如Le y -3FL和Le y -Le x -3FL。与Lac相比，对Fucα1,2LacNAc和LacNAc的优先岩藻糖基化活性使可编程岩藻糖基化成为可能，从而一锅合成KH-1抗原。
• Chemo-enzymatic synthesis of functionalized oligomers of N-acetyllactosamine glycan derivatives and their immobilization on biomaterial surfaces
  作者：Kathrin Adamiak、Thorsten Anders、Manja Henze、Helmut Keul、Martin Möller、Lothar Elling

  DOI：10.1016/j.molcatb.2012.02.002

  日期：2012.12

  Poly-N-acetyllactosamines (poly-LacNAc, [-3Gal(beta 1-4)GlcNAc(beta 1-](n)) are terminal glycan structures present in glycoproteins and glycolipids. Their biological functions as ligands for galectins and as carriers of glycan epitopes are well documented. In the present paper we have characterized six novel functionalized beta-D-GlcNAc derivatives, including aglyca of varying hydrophobicity and molecular weight, as substrates for recombinant human beta 1,4 galactosyltransferase 1 (beta 4GalT-1). The sugar derivatives carry short or long amino- or azide-terminated linker molecules for further modification or immobilization. The linker chemistry had an impact on enzyme kinetics and enzymatic syntheses of N-acetyllactosamine derivatives (LacNAc, Gal(beta 1-4)GlcNAc(beta 1-R). The combination of beta 4GaIT-1 with bacterial beta 1,3-N-acetylglucosaminyltransferase (beta 3GlcNAc-T) resulted in the preparative syntheses of LacNAc oligomers with up to three LacNAc repeating units. All products were characterized by NMR and MS. The obtained LacNAc glycans were immobilized onto microtiter plates and their efficiency of binding of fungal galectin CGL2 was determined. (C) 2012 Elsevier B.V. All rights reserved.
• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.