octyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside | 222057-25-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-6-octoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 222057-25-2
• 化学式: C₃₅H₄₆O₆
• 分子量: 562.747
• InChiKey: JNWPVUDLGFITDN-VABIIVNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  octyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 palladium dihydroxide 咪唑 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 octyl 3-deoxy-α-D-arabino-hexopyranosyl-(1->6)-α-D-mannopyranoside
  参考文献：
  名称：

  辛基α-d-甘露吡喃糖基-（1→6）-α-d-甘露吡喃糖苷的脱氧和甲氧基类似物的合成作为分枝杆菌脂阿拉伯糖甘露聚糖生物合成的探针

  摘要：

  摘要涉及二糖α-d -Man p-（1→6）-α-d -Man p -OOctyl的一组类似物，这是一种依赖于戊二烯单磷酸甘露糖依赖性α-（1→6）-甘露糖基转移酶的已知受体底物在组装的过程中，已经合成了分枝杆菌脂肪阿拉伯甘露聚糖的α-（1→6）-连接的甘露聚糖核心。描述了到目标脱氧和甲氧基类似物的合成路线，其中母体二糖的羟基之一已被修饰。所有糖基化反应都涉及使用碘鎓离子活化来使用辛基糖苷受体和硫糖苷供体，并且通过测量1 J C-1，H-1确定了形成的甘露吡喃糖苷键的立体化学。取决于目标，关键的甲基化或脱氧反应是在单糖或双糖底物上进行的。

  DOI：

  10.1016/j.carres.2007.05.001
• 作为产物：
  描述：

  octyl α-D-mannopyranoside 在 吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.58h， 生成 octyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Novel synthetic (1 → 6)-α-d-mannodisaccharide substrates support processive mannosylation catalysed by the mycobacterial cell envelope enzyme fraction

  摘要：

  研究人员合成并在霉菌甘露糖基转移酶试验中筛选了三种新的、具有环己基烷基或辛基磺酰基类似琼酮功能的（1-α-6）-δ-D-甘露二糖。2-Cyclohexylethyl (1 â 6)-α-D-Man2 是最佳的受体底物，而磺酰基则大大降低了甘露二糖作为受体的能力。尽管存在这些差异，但质谱分析证实，所有合成甘露二糖苷都能接受多达十个额外的甘露糖单位，也就是说，转移不受琼脂糖类型的影响。本文报告的结果表明，负责连续甘露糖连接的酶是存在于分枝杆菌细胞包膜无细胞系统中的δ-甘露糖基转移酶。

  DOI：

  10.1039/c3ra43575j

文献信息

• Synthesis of alkyl and cycloalkyl α-d-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay
  作者：Monika Poláková、Martina Beláňová、Ladislav Petruš、Katarína Mikušová

  DOI：10.1016/j.carres.2010.03.011

  日期：2010.7

  The synthesis of a series of alkyl (having from C6 to C20 aglycones), cyclohexyl, and cyclohexylalkyl alpha-d-mannopyranosides, 6-deoxygenated analogs, thioglycosides, and sulfones derived thereof, is reported. Here, under the in vitro assay conditions used, none of the 15 tested compounds acted as an inhibitor of the mannose transfer catalyzed by the enzymes present in mycobacterial membrane and cell

  据报道，合成了一系列烷基（具有从C 6至C 20的糖苷配基），环己基和环己基烷基α-d-甘露吡喃糖苷，6-脱氧类似物，硫代糖苷及其衍生的砜。在此，在所用的体外测定条件下，15种被测化合物均未充当分枝杆菌膜和细胞壁组分中存在的酶催化的甘露糖转移的抑制剂。在分枝杆菌甘露糖基转移酶反应中，包含较短的脂族，最多8个碳原子长的线性或环状糖苷的甘露吡喃糖苷用作受体底物。与砜相反，该硫糖苷表现出相似的行为，而后者基本上未被分枝杆菌酶所识别。6-脱氧糖苷未被酶处理，
• Epimeric and amino disaccharide analogs as probes of an α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannanbiosynthesis
  作者：Pui Hang Tam、Todd L. Lowary

  DOI：10.1039/b916580k

  日期：——

  Mycobacterial lipoarabinomannan (LAM) is an important, immunologically active glycan found in the cell wall of mycobacteria, including the human pathogen Mycobacterium tuberculosis. At the core of LAM is a mannan domain comprised of α-(1→6)-linked-mannopyranose (Manp) residues. Previously, we and others have demonstrated that α-Manp-(1→6)-α-Manp disaccharides (e.g., Manp-(1→6)-α-ManpOctyl, 1) are the

  分枝杆菌脂阿拉伯甘露聚糖 （我是）是重要的，具有免疫活性的 聚糖 在分枝杆菌的细胞壁中发现，包括人类病原体 分枝杆菌肺结核。的核心我是 是由α-（1→6）-连接的-甘露吡喃糖 （人p）残留物。此前，我们和其他人已经表明，α-曼p - （1→6）-α-曼p二糖（例如，曼p-（1→6）-α-曼p辛基，1）是参与LAM甘露聚糖核心组装的酶的最小受体底物。我们在这里报告的合成5差向异构体和三个氨基的类似物1，以及它们随后的生化评估针对α-（1→6）-ManT活性存在于膜制备从耻垢分枝杆菌。改变甘露-的任残基的构型1至距骨-或葡萄糖-导致的减少或丧失活性，从而证实显示的早期工作，在C-2和C-4 羟每个单糖的组对于酶识别很重要。由这些类似物形成的产物的表征是结合使用质谱和糖苷酶消化和完整的底物动力学也进行了。如所预期的，其中受体羟基已被氨基取代的类似物不是酶的底物，而是弱抑制剂。
• Ravindranathan Kartha; Field, Synlett, 1999, # 3, p. 311 - 312
  作者：Ravindranathan Kartha、Field

  DOI：——

  日期：——
• Modified mannose disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesis
  作者：Vinodhkumar Subramaniam、Sudagar S. Gurcha、Gurdyal S. Besra、Todd L. Lowary

  DOI：10.1016/j.bmc.2004.11.027

  日期：2005.2

  A panel of alpha-(1 6)-linked mannose disaccharides (5-8) in which the 2'-OH group has been replaced, independently, by deoxy, fluoro, amino, and methoxy functionalities has been synthesized. Evaluation of these compounds as potential substrates or inhibitors of a polyprenol monophosphomannose-dependent alpha-(1-6)-mannosyltransferase involved in mycobacterial LAM biosynthesis demonstrated that the enzyme is somewhat tolerant substitution at this site. The enzyme recognizes the disaccharides with groups similar or smaller in size than the native hydroxyl (6-8), but not the disaccharide with the more sterically demanding methoxy group (5). The 2'-OH appears not form a critical hydrogen bonding interaction with the protein as the 2'-deoxy analog is a substrate for the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthetic disaccharide analogs as potential substrates and inhibitors of a mycobacterial polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase
  作者：Vinodhkumar Subramaniam、Sudagar S. Gurcha、Gurdyal S. Besra、Todd L. Lowary

  DOI：10.1016/j.tetasy.2004.11.063

  日期：2005.1

  Analogs of the alpha-D-Manp-(1 --> 6)-alpha-D-Manp-O(CH2)(7)CH3 disaccharide 4, a known substrate for a polyprenol monophosphomannose-dependent alpha-(1-->6)-mannosyltransferase involved in mycobacterial LAM biosynthesis, have been synthesized and screened as potential substrates and inhibitors of the enzyme. In the disaccharides synthesized, the hydroxyl groups at C-2 and C-6 on the reducing end residue have been replaced by combinations of amino, fluoro, and methoxy functionalities 9-14. In addition, a disaccharide in which the nonreducing mannopyranose residue was replaced with a 3,6-anhydromannopyranose residue 34 was synthesized from a byproduct formed during one of the reactions leading to 14. When tested against the enzyme, none were active as substrates, as would be expected as all lack the C-6' hydroxyl group to which, an additional sugar residue would be transferred. Evaluation of these compounds as inhibitors of the enzyme revealed that only three, 11, 12, and 13, all of which contain one or more amino groups, inhibited the enzyme. The most potent inhibitor was the diamino-disaccharide, 11. (C) 2004 Elsevier Ltd. All rights reserved.