11-(anthracen-9-ylmethoxy)undecan-1-ol | 1418214-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11-(anthracen-9-ylmethoxy)undecan-1-ol
• 英文别名: 11-[(9'-anthracenyl)methoxy]undecan-1-ol
• CAS: 1418214-04-6
• 化学式: C₂₆H₃₄O₂
• 分子量: 378.555
• InChiKey: CQKOXGKAMBWKOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  28.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  11-(anthracen-9-ylmethoxy)undecan-1-ol 在 盐酸 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 6.0h， 生成 diisopropylammonium 11-(9-anthracenylmethoxy)undecyl phosphoroimidazolidate
  参考文献：
  名称：

  Synthesis of a fluorescent acceptor substrate for glycosyltransferases involved in the assembly of O-antigens of enterohemorrhagic Escherichia coli O157 and O5

  摘要：

  The assembly of the repeating units of O-antigens in Gram negative bacteria is catalyzed by specific glycosyltransferases. Previously we used GlcNAc/GalNAc alpha-diphosphate-phenoxyundecyl as natural acceptor substrate analogs in assays of the transfer of radioactive sugars by bacterial glycosyltransferases. In order to develop new, fluorescence based assays we have synthesized a fluorescent acceptor P-1-[11-(anthracen-9-ylmethoxy)undecyl]-P-2-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl) diphosphate and have shown that the compound was an excellent acceptor for glucosyltransferase WbdN from Escherichia coli (E. coli) O157 and for galactosyltransferase WbwC from E. coli O5. This is the first report of the Galtransferase activity of the wbwC gene product of E. coli O5. The presence of the fluorescent label in the acceptor molecule allows the detection of glycosyltransferase reaction products with high sensitivity, eliminating the need for radioactive nucleotide sugars. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.009
• 作为产物：
  描述：

  11-[(9'-anthracenyl)methoxy]undec-1-ene 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以55%的产率得到11-(anthracen-9-ylmethoxy)undecan-1-ol
  参考文献：
  名称：

  Synthesis and acceptor properties of 11-[(9′-Anthracenyl)methoxy]undecyl Phosphate and P 1-{11-[(9′-anthracenyl)methoxy]undecyl}-P 2-(α-D-galactopyranosyl) diphosphate in enzymatic reactions catalyzed with galactosylphosphotransferase and mannosyltransferase from Salmonella newport

  摘要：

  Derivatives of undecyl phosphate containing the fluorescent label-11-[(9'-anthracenyl)methoxy]undecyl phosphate and P (1)-{11-[(9'-anthracenyl)methoxy]undecyl}-P (2)-(alpha-D-galactopyranosyl) diphosphate-were synthesized for the first time. An ability of the substituted undecyl phosphate to serve as an acceptor substrate of the galactosyl phosphate residue, and of the respective galactosyl diphosphate derivative as an acceptor substrate of the mannose residue in the reactions catalyzed with galactosylphosphotransferase and mannosyltransferase of the membrane preparation from Salmonella newport cells, respectively, was shown.

  DOI：

  10.1134/s1068162013010123