octyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside | 849465-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: octyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside
• CAS: 849465-31-2
• 化学式: C₅₄H₆₀O₆
• 分子量: 805.067
• InChiKey: IHRBFCDOWBXTJT-FERWHMKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.85
• 重原子数：
  60.0
• 可旋转键数：
  23.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  octyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 octyl 2-azido-2-deoxy-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Modified mannose disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesis

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.11.027
• 作为产物：
  描述：

  octyl α-D-mannopyranoside 在 吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 octyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside
  参考文献：
  名称：

  Modified mannose disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesis

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.11.027

文献信息

• Novel synthetic (1 → 6)-α-d-mannodisaccharide substrates support processive mannosylation catalysed by the mycobacterial cell envelope enzyme fraction
  作者：Erika Lattová、Zuzana Svetlíková、Katarína Mikušová、Helene Perreault、Monika Poláková

  DOI：10.1039/c3ra43575j

  日期：——

  Three new (1 → 6)-α-D-mannodisaccharides with cyclohexylalkyl or octylsulfonyl function like aglycone were synthesized and screened in the mycobacterial mannosyltransferase assay. 2-Cyclohexylethyl (1 → 6)-α-D-Man2 acted as the best acceptor substrate, whereas the sulfonyl group significantly reduced the ability of the mannodisaccharide to serve as the acceptor. Despite these differences, mass spectrometric analysis confirmed the capability of all synthetic mannodisacharides to accept up to ten additional mannose units, i.e. the transfer was not affected by the type of aglycone. The results reported here suggest that the enzyme responsible for the consecutive mannose attachment is the processive α-mannopyranosyltransferase present in the cell-free system of the mycobacterial cell envelope.

  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。