ammonium-C-(1-deoxy-α-D-galactopyranosyl)methanephosphonate | 82701-50-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ammonium-C-(1-deoxy-α-D-galactopyranosyl)methanephosphonate
• CAS: 82701-50-6
• 化学式: C₇H₁₅O₈P*H₃N
• 分子量: 275.196
• InChiKey: PRRAGPADROIWGG-SLCGNBMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.83
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  182.68
• 氢给体数：
  7.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ammonium-C-(1-deoxy-α-D-galactopyranosyl)methanephosphonate 、 胸苷-5'-三磷酸 在 magnesium chloride 作用下， 以 tris-HCl-buffer 为溶剂， 反应 6.0h， 以6.8 mg的产率得到
  参考文献：
  名称：

  Enzyme-catalyzed synthesis of isosteric phosphono-analogues of sugar nucleotides

  摘要：

  利用胸苷酰基转移酶，已经成功实现了糖核苷酸等效磷酸类似物的酶促高效合成。

  DOI：

  10.1039/b808078j
• 作为产物：
  描述：

  Diethyl 2,6-anhydro-1-deoxy-3,4,5,7-tetra-O-benzyl-L-glycero-D-gluco-heptulopyranose-1-phosphonate 在 碘代三甲硅烷 、 Amberlite IR-120 (H+) 、 氨 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以100%的产率得到ammonium-C-(1-deoxy-α-D-galactopyranosyl)methanephosphonate
  参考文献：
  名称：

  Enzyme-catalyzed synthesis of isosteric phosphono-analogues of sugar nucleotides

  摘要：

  利用胸苷酰基转移酶，已经成功实现了糖核苷酸等效磷酸类似物的酶促高效合成。

  DOI：

  10.1039/b808078j

文献信息

• Thiophosphate and thiophosphonate analogues of glucose-1-phosphate: synthesis and enzymatic activity with a thymidylyltransferase
  作者：Matthew W. Loranger、Stephen A. Beaton、Katie L. Lines、David L. Jakeman

  DOI：10.1016/j.carres.2013.06.007

  日期：2013.9

  Synthetic methods were investigated for the preparation of O and S-glucosyl thiophosphates and glucosyl 1C-thiophosphonate. Four protected glucosyl thiophosphate compounds were synthesized and characterized as precursors to glucose 1-thiophosphate. The effect of various reaction conditions and the nature of the carbohydrate and thiophosphate protecting groups and how they impact both the yields and alpha/beta diastereoselectivity of the glucosyl thiophosphate products were explored. A novel isomerization from an O-linked to S-linked glucosyl thiophosphate was observed. alpha-D-Glucose-1C-thiophosphonate was synthesized and evaluated as a substrate for the thymidylyltransferase, Cps2L. Tandem mass spectrometric analysis determined the position of sulfur in the sugar nucleotide product. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.