(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(phosphonooxy)-5-propiolamidotetrahydro-2H-pyran-3,4-diyl diacetate | 1376665-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(phosphonooxy)-5-propiolamidotetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 1376665-42-7
• 化学式: C₁₅H₂₀NO₁₂P
• 分子量: 437.297
• InChiKey: MLOJSVOMPZOMHL-TVKJYDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.63
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  183.99
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(phosphonooxy)-5-propiolamidotetrahydro-2H-pyran-3,4-diyl diacetate 在 1,4-dithio-D,L-threitol 、 sodium methylate 、 magnesium chloride 作用下， 以 甲醇 为溶剂， 反应 49.0h， 生成 P'-[2-(1-oxo-2-propyn-1-yl)amino-2-deoxy-α-D-galactopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Uridine Diphosphate-GlcNAc and Uridine Diphosphate-GalNAc Analogs for the Preparation of Unnatural Glycosaminoglycans

  摘要：

  Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

  DOI：

  10.1021/jo202322k
• 作为产物：
  描述：

  (3R,4R,5R,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride 在 磷酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(phosphonooxy)-5-propiolamidotetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Uridine Diphosphate-GlcNAc and Uridine Diphosphate-GalNAc Analogs for the Preparation of Unnatural Glycosaminoglycans

  摘要：

  Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

  DOI：

  10.1021/jo202322k