pent-4-enyl 5-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside | 765274-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 5-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
• 英文别名: pent-4-enyl 6-O-(2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
• CAS: 765274-11-1
• 化学式: C₄₃H₄₆O₁₁
• 分子量: 738.832
• InChiKey: OFFRENJYTOIOHB-KLMVDSGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  54.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  128.21
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 5-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside 在 甲醇 、 氨 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 pent-4-enyl 5-O-(α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Development of a plate-based scintillation proximity assay for the mycobacterial AftB enzyme involved in cell wall arabinan biosynthesis

  摘要：

  A number of mycobacterial arabinosyltransferases, such as the Emb proteins, AftA, AftB, AftC, and AftD have been characterized and implicated to be involved in the cell wall arabinan assembly. These arabinosyltransferases are essential for the viability of the organism and are logically valid targets for developing new anti-tuberculosis agents. For instance, Ethambutol, a first line anti-tuberculosis drug, targets the Emb proteins involved in the formation of the arabinan of cell wall arabinogalactan. Among these arabinosyltransferases, the terminal beta-(1 -> 2) arabinosyltransferase activity has been associated with AftB. The predicted topology of AftB in Mycobacterium tuberculosis has 10 N terminal transmembrane domains and a C terminal hydrophilic domain similar to the Emb proteins. It has a conserved GT-C motif and is difficult to express. In a cell free assay, synthetic disaccharide, alpha-D-Araf-(1 -> 5)-alpha-D- Araf-octyl, has been used as a substrate to explore the function of AftB. In our work, the disaccharide was synthesized in its pentenylated and biotinylated form, and the enzymatic product formed was identified as the beta-(1 -> 2) arabinofuranose adduct. When synthetic tri- and tetra-saccharides were used as substrates, a mixture of products containing both beta-(1 -> 2) and alpha-(1 -> 5) linkages were formed. Therefore, the biotinylated disaccharide was selected to develop a scintillation proximity assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.040
• 作为产物：
  描述：

  2,3,5-三-O-苯甲酰基-alpha-D-阿拉伯呋喃糖基溴化物 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.5h， 生成 pent-4-enyl 5-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  正戊烯基阿拉伯呋喃糖基供体的制备，性质和应用。

  摘要：

  [反应：见正文]已使用阿拉伯糖作为模型测试了正戊烯基呋喃糖基供体的发育。易于制备的原酸酯（NPOE）被转化为脱甲（NPG（ACK）），然后被武装（NPG（ALK））正戊烯基阿拉伯呋喃糖苷。这些呋喃糖基供体和吡喃糖基对应物的反应性已经通过允许两者成对竞争竞争受体来评估。对于NPOE和武装（NPG（ALK））对，从供体中获得偶联产物，而对于解除武装（NPG（AC））对，仅获得阿拉伯呋喃诺偶联产物。为了探究其合成用途，已证明NPOE是制备结核分枝杆菌复杂lipoarabinomannan细胞壁阵列的α-1,5-连接的阿拉伯聚糖片段所需的唯一前体。

  DOI：

  10.1021/ol0490680

文献信息

• Synthesis of a Core Arabinomannan Oligosaccharide of <i>Mycobacterium tuberculosis</i>
  作者：Alexandra Hölemann、Bridget L. Stocker、Peter H. Seeberger

  DOI：10.1021/jo061233x

  日期：2006.10.1

  The synthesis of a core arabinomannan (AM) oligosaccharide from Mycobacterium tuberculosis has been achieved using a convergent [6 + 6] glycosylation strategy and a defined set of building blocks. Dodecasaccharide 1, containing the key AM structural features of lipoarabinomannan (LAM), was obtained in excellent yield and selectivity from hexamannan 3 and hexaarabinan 5. This flexible synthetic strategy involves late-stage couplings and modifications, thus providing ready access to several different LAM fragments. The incorporation of a thiol linker at the reducing end of the oligosaccharide allows for the attachment of these compounds to microarrays and protein carriers.