octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranoside | 187140-06-3

• 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 α-D-mannopyranosyl-(1->6)-α-D-mannopyranoside
• 英文别名: Man(a1-6)Man(a)-O-octyl；(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-octoxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 187140-06-3
• 化学式: C₂₀H₃₈O₁₁
• 分子量: 454.515
• InChiKey: QOIDJNQXSBGPJA-KTTIQVEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  decaprenylphosphoryl arabinose 、 octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranoside 在 arabinosyltransferase 作用下， 生成
  参考文献：
  名称：

  Identification of a Novel Mycobacterial Arabinosyltransferase Activity Which Adds an Arabinosyl Residue to α-d-Mannosyl Residues

  摘要：

  The arabinosyltransferases responsible for the biosyntheis of the arabinan domains of two abundant heteropolysaccharides of the cell envelope of all mycobacterial species, lipoarabinomannan and arabinogalactan, are validated drug targets. Using a cell envelope preparation from Mycobacterium smegmatis as the enzyme source and di- and trimannoside synthetic acceptors, we uncovered a previously undetected,arabinosyltransferase activity. Thin layer chromatography, GC/MS, and LC/MS/MS analyses of the major enzymatic product are consistent with the transfer of an arabinose residue to the 6 position of the terminal mannosyl residue at the nonreducing end of the acceptors: The newly identified enzymatic activity is resistant to ethambutol and could correspond to are priming arabinosyl transfer reaction that occurs during lipoarabinomannan biosynthesis.

  DOI：

  10.1021/acschembio.6b00093
• 作为产物：
  描述：

  octyl α-D-mannopyranoside 在 吡啶 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 61.08h， 生成 octyl α-D-mannopyranosyl-(1->6)-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

• Rapid, iterative assembly of octyl α-1,6-oligomannosides and their 6-deoxy equivalents
  作者：Jacinta A. Watt、Spencer J. Williams

  DOI：10.1039/b503919c

  日期：——

  Mycobacterium tuberculosis is the cause of the deadly human disease tuberculosis. In studies over the last 40 years it has been revealed that this organism possesses a complex cell wall including glycophospholipids such as the phosphatidylinositiol mannosides (PIMs), lipomannan (LM) and lipoarabinomannan (LAM). These glycolipids all contain a common α-1,6-linked mannoside core, and the higher PIMs and LAM possess α-1,2-linked mannosyl residues. It has been shown that simple α-1,6-linked oligomannosides can act as substrates for α-1,6-mannosyltransferases in mycobacteria. Here we report a simple iterative synthesis of a series of hydrophobic octyl α-1,6-linked oligomannosides from mono- through to tetrasaccharides. We have utilized a single thioglycoside donor and alcohol acceptor. Further, we have developed conditions for the conversion of each of these compounds to the 6-deoxy congeners. Deoxygenation of the 6-position of the terminal mannosyl residue should prevent these compounds acting as substrates for the abundant α-1,6-mannosyltransferases in mycobacteria and should permit detection of the elusive α-1,2-mannosyltransferase activity responsible for elaboration of LM to mature LAM and the biosynthesis of the higher PIMs.

  结核分枝杆菌（Mycobacterium tuberculosis）是导致致命的人类疾病结核病的原因。在过去40年的研究中，已揭示这种微生物拥有一个复杂的细胞壁，其中包括糖磷脂类，如磷脂酰肌醇甘露醇（PIMs）、脂甘露醇（LM）和脂阿拉伯甘露醇（LAM）。这些糖脂都含有一个共同的α-1,6-链接的甘露糖核，而高级的PIMs和LAM则具有α-1,2-链接的甘露糖残基。已有研究表明，简单的α-1,6-链接的寡甘露糖可以作为分枝杆菌中α-1,6-甘露糖基转移酶的底物。在这里，我们报告了一种简单的迭代合成方法，用于制备一系列疏水的辛基α-1,6-链接的寡甘露糖，从单糖到四糖。我们使用了一个单一的硫代糖供体和醇受体。此外，我们还开发了将这些化合物转化为6-脱氧类似物的条件。终端甘露糖残基的6-位脱氧应防止这些化合物作为分枝杆菌中丰富的α-1,6-甘露糖基转移酶的底物，并应允许检测到负责将LM精细化为成熟的LAM以及高级PIMs生物合成的难以捉摸的α-1,2-甘露糖基转移酶活性。
• 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，
• Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases
  作者：T Ziegler

  DOI：10.1016/s0008-6215(96)00215-7

  日期：1996.12.13

  Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MIT at 1.4, MIT at 1.2, and MIT at 1.5, respectively. (C) 1996 Elsevier Science Ltd.
• Synthetic mannosides act as acceptors for mycobacterial α1-6 mannosyltransferase
  作者：Jillian R Brown、Robert A Field、Adam Barker、Mark Guy、Ravinder Grewal、Kay-Hooi Khoo、Patrick J Brennan、Gurdyal S Besra、Delphi Chatterjee

  DOI：10.1016/s0968-0896(00)00300-x

  日期：2001.4

  A series of synthetic mannosides was screened in a cell-free system for their ability to act as acceptor substrates For mycobacterial mannosyltransferases. Evaluation of these compounds demonstrated the incorporation of [C-14]Man From GDP-[C-14]Man into a radiolabeled organic-soluble fraction and analysis by thin layer chromatography and autoradiography revealed the formation of two radiolabeled products. Each synthetic acceptor was capable of accepting one or two mannose residues. resulting in a major and a minor mannosylated product. Both products from each acceptor were isolated and their mass was confirmed by fast-atom bombardment-mass spectrometry (FABMS). Characterization of each mannosylated product by exo-glycosidase digestion, acetolysis and linkage analysis by gas chromatography-mass spectrometry of partially per-O-methylated alditols, revealed only alpha1-6-linked products. In addition, the antibiotic amphomycin selectively inhibited the formation of mannosylated products suggesting polyprenolmonophosphate-mannose (C-35 (50)-P-Man) was the immediate mannose donor in all mannosylation reactions observed. The ability of synthetic disaccharides to act as acceptor substrates in this system, is most Likely due to the action of a mycobacterial polyprenol-P-Man:mannan alpha1-6 mannosyltransferase involved in the biosynthesis of linear alpha1-6-linked lipomannan. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.