2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide | 114718-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide
• 英文别名: [(2R,3S,4S,5S,6S)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate
• CAS: 114718-45-5
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: CYAYKKUWALRRPA-IKOXMDCHSA-N

物化性质

• 沸点：
  412.0±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide 在 sodium methylate 、 caesium carbonate 、 sodium sulfate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2S,3R,4S,5R,6R)-2-[6'-(diethylamino)spiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold

  摘要：

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.

  DOI：

  10.1021/ja204781t

文献信息

• FLUORESCENT PROBE
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20150212073A1

  公开（公告）日：2015-07-30

  A compound represented by the formula (I) [R 1 represents hydrogen atom or a substituent; R 2 , R 3 , R 6 , and R 7 represent hydrogen atom, an alkyl group, a halogen atom, or a hydrophilic substituent; R 4 and R 5 represent an alkyl group or an aryl group; R 8 and R 9 represent a group cleaved by contact with an object substance for measurement; and X represents silicon atom, germanium atom, or tin atom] or a salt thereof, which is useful as a fluorescent probe that emits red fluorescence by contact with an object substance for measurement.

  化合物的化学式为（I）[R1代表氢原子或取代基；R2、R3、R6和R7代表氢原子、烷基、卤素原子或亲水性取代基；R4和R5代表烷基或芳基；R8和R9代表通过与物质接触测量而裂解的基团；X代表硅原子、锗原子或锡原子]或其盐，该化合物可用作荧光探针，通过与物质接触测量而发出红色荧光。
• GIESE, B.;DUPUIS, J., TETRAHEDRON LETT., 1984, 25, N 13, 1349-1352
  作者：GIESE, B.、DUPUIS, J.

  DOI：——

  日期：——
• US9250232B2
  申请人：——

  公开号：US9250232B2

  公开（公告）日：2016-02-02