2-deoxy-2-[(1-oxo-2-propen-1-yl)amino]-α-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate) | 1355005-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-[(1-oxo-2-propen-1-yl)amino]-α-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate)
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-phosphonooxy-5-(prop-2-enoylamino)oxan-2-yl]methyl acetate
• CAS: 1355005-44-5
• 化学式: C₁₅H₂₂NO₁₂P
• 分子量: 439.313
• InChiKey: KBLIIXQSRVPFFQ-DIAXPKBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-[(1-oxo-2-propen-1-yl)amino]-α-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到2-deoxy-2-[(1-oxo-2-propen-1-yl)amino]-α-D-glucopyranose-1-(dihydrogen phosphate) 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：

  1,3,4,6-tetra-O-acetyl-2-acrylamido-2-deoxy-D-glucose 在 磷酸 作用下， 反应 2.0h， 以23%的产率得到2-deoxy-2-[(1-oxo-2-propen-1-yl)amino]-α-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate)
  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