dibenzyl (2-acetonyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl) phosphate | 652158-60-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: dibenzyl (2-acetonyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl) phosphate
• 英文别名: dibenzyl(2-acetonyl-2-deoxy-3,4,5-tri-O-acetyl-α-D-galactopyranosyl)phosphate；dibenzyl (2-acetonyl-deoxy-3,4,5-tri-O-acetyl-α-D-galactopyranosyl)phophate；[(2R,3R,4R,5R,6R)-3,4-diacetyloxy-6-bis(phenylmethoxy)phosphoryloxy-5-(2-oxopropyl)oxan-2-yl]methyl acetate
• CAS: 652158-60-6
• 化学式: C₂₉H₃₅O₁₂P
• 分子量: 606.563
• InChiKey: IAEZEJSQTADPTK-SXEGYFPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  dibenzyl (2-acetonyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl) phosphate 在 palladium 10% on activated carbon 四氮唑 、 氢气 作用下， 以 吡啶 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 92.0h， 生成
  参考文献：
  名称：

  [EN] TARGETED CONJUGATES WITH A MODIFIED SACCHARIDE LINKER
  [FR] SYSTEME D'ADMINISTRATION CIBLEE POUR AGENTS BIOACTIFS

  摘要：

  公开号：

  WO2005051429A3
• 作为产物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 dibenzyl (2-acetonyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl) phosphate
  参考文献：
  名称：

  A Chemoenzymatic Approach toward the Rapid and Sensitive Detection of O-GlcNAc Posttranslational Modifications

  摘要：

  We report a new chemoenzymatic strategy for the rapid and sensitive detection of O-GlcNAc posttranslational modifications. The approach exploits the ability of an engineered mutant of beta-1,4-galactosyltransferase to selectively transfer an unnatural ketone functionality onto O-GlcNAc glycosylated proteins. Once transferred, the ketone moiety serves as a versatile handle for the attachment of biotin, thereby enabling chemiluminescent detection of the modified protein. Importantly, this approach permits the rapid visualization of proteins that are at the limits of detection using traditional methods. Moreover, it bypasses the need for radioactive precursors and captures the glycosylated species without perturbing metabolic pathways. We anticipate that this general chemoenzymatic strategy will have broad application to the study of posttranslational modifications.

  DOI：

  10.1021/ja038545r

文献信息

• Stereoselective synthesis of UDP-2-(2-ketopropyl)galactose aided by di-tert-butylsilylene protecting group
  作者：Yasuharu Sakamoto、Tsuyoshi Ohta、Yukishige Ito

  DOI：10.1007/s10719-015-9581-y

  日期：2015.10

  UDP-2-(2-ketopropyl)galactose (1) has been utilized as a valuable probe for profiling proteins modified by O-GlcNAc. In this work, we developed a protocol for efficient synthesis of 1. Thus, 2-methallylgalactose derivative 11, a synthetic intermediate for the compound 1, was prepared by stereoselective iodination and methallylation at C-2 position, through exploitation of 4,6-O-di-tert-butylsilylene protecting group.

  UDP-2-(2-酮丙基)半乳糖（1）被用作探测O-GlcNAc修饰蛋白的重要工具。在本研究中，我们开发了一种高效合成1的方案。因此，通过在C-2位进行立体选择性碘化和甲基丙烯基化的方式，利用4,6-O-二叔丁基硅烷保护基，制备了化合物1的合成中间体2-甲烯基半乳糖衍生物11。
• Improved synthesis of UDP-2-(2-ketopropyl)galactose and a first synthesis of UDP-2-(2-ketopropyl)glucose for the site-specific linking of biomolecules via modified glycan residues using glycosyltransferases
  作者：Andrés E. Dulcey、Pradman K. Qasba、Jeffrey Lamb、Gary L. Griffiths

  DOI：10.1016/j.tet.2011.01.081

  日期：2011.3

  The potential of wild-type and mutant glycosyltransferases to produce glycoconjugates carrying sugar moieties with chemical handles has made it possible to conjugate biomelecules with orthogonal reacting groups at specific sites. The synthesis of UDP-2-(2-ketopropyl)galactose has been previously carried out, albeit with difficulty and low efficiency. A modified approach has been developed for the synthesis of UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose, allowing better access to the desired test compounds, the UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose analogs were synthesized in eight steps and 4.8% and 5.3% overall yield, respectively, an improvement over the first generation synthesis involving eight steps and an overall yield of 0.7%. Published by Elsevier Ltd.