(3R,4R,5R,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride | 1355005-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride
• 英文别名: 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-D-galactopyranose HCl；[(2R,3R,4R,5R)-3,4,6-triacetyloxy-5-aminooxan-2-yl]methyl acetate;hydrochloride
• CAS: 1355005-40-1
• 化学式: C₁₄H₂₁NO₉*ClH
• 分子量: 383.783
• InChiKey: BQLUYAHMYOLHBX-ALSBSFMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  25
• 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：
  140
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-carbobenzyloxyamino-2-deoxy-D-galactopyranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢气 、 palladium(II) hydroxide 作用下， 生成 (3R,4R,5R,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride
  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

文献信息

• [EN] BIVALENT TARGETED CONJUGATES<br/>[FR] CONJUGUÉS CIBLÉS BIVALENTS
  申请人：ARBUTUS BIOPHARMA CORP

  公开号：WO2020093053A1

  公开（公告）日：2020-05-07

  The invention provides conjugates that comprise a bivalent targeting moiety, a nucleic acid, and optional linking groups as well as synthetic intermediates and synthetic methods useful for preparing the conjugates, compositions comprising the bidentate targeting ligands and the conjugates, as well as methods for targeting therapeutic nucleic acids with the bidentate conjugates. The conjugates are useful to target therapeutic nucleic acids.

  这项发明提供了包括双价靶向基团、核酸和可选连接基团的共轭物，以及用于制备这些共轭物的合成中间体和合成方法，包括含有双齿靶向配体和共轭物的组合物，以及使用双齿共轭物靶向治疗性核酸的方法。这些共轭物可用于靶向治疗性核酸。
• Diazo group as a new chemical reporter for bioorthogonal labelling of biomolecules
  作者：Laia Josa-Culleré、Yelena A. Wainman、Kevin M. Brindle、Finian J. Leeper

  DOI：10.1039/c4ra08861a

  日期：——

  spontaneous cycloaddition reactions with strained alkenes and alkynes. The rates of reaction are similar to the equivalent reactions of azide groups. This allows diazo groups to be used as bioorthogonal reporter groups. This is demonstrated by fluorescent labelling of a diazoacetylated protein and of cell-surface glycans via metabolic incorporation of a diazoacetylated sugar.

  重氮乙酰基已显示出与应变烯烃和炔烃发生自发的环加成反应。反应速率类似于叠氮化物基团的等效反应。这允许重氮基团用作生物正交的报告基团。通过重氮乙酰化糖的代谢掺入对重氮乙酰化的蛋白质和细胞表面聚糖进行荧光标记证明了这一点。
• WO2020093061A5
  申请人：——

  公开号：WO2020093061A5

  公开（公告）日：2022-11-07
• BIVALENT TARGETED CONJUGATES
  申请人：Arbutus Biopharma Corporation

  公开号：EP3873486A1

  公开（公告）日：2021-09-08
• THERAPEUTIC METHODS
  申请人：Genevant Sciences GmbH

  公开号：EP3873530A1

  公开（公告）日：2021-09-08