1-O-(3-azidoopropyl)-β-D-glucopyranuronic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(3-azidoopropyl)-β-D-glucopyranuronic acid
• 英文别名: 1-O-(3-azidopropyl)-β-D-glucopyranuronic acid；3-azido-propyl-β-D-glucopyranosiduronic acid；1-O-(3-azidopropyl)--D-glucopyranuronic acid；D-GlcAβProN₃；(2S,3S,4S,5R,6R)-6-(3-azidopropoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₉H₁₅N₃O₇
• 分子量: 277.234
• InChiKey: DYHZUDMSHIRDOJ-KPRJIFDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-(3-azidoopropyl)-β-D-glucopyranuronic acid 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3-aminopropyl β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide

  摘要：

  通过一种简便的化学酶法，以一锅多酶的方式合成了生物素化的肝素六糖。

  DOI：

  10.1039/c5ob00462d
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 在 sodium azide 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1-O-(3-azidoopropyl)-β-D-glucopyranuronic acid
  参考文献：
  名称：

  使用顺序一锅多酶系统定制设计和合成硫酸乙酰肝素低聚糖类似物

  摘要：

  硫酸乙酰肝素类似物：已经开发出高效的一锅多酶（OPME）化学酶系统，用于激活和转移N-乙酰氨基葡萄糖（GlcNAc）和葡萄糖醛酸（GlcA）。它们被应用于硫酸乙酰肝素寡糖的N-硫酸化类似物的连续定制合成，这可能是潜在的治疗方法。

  DOI：

  10.1002/anie.201305667

文献信息

• CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140235575A1

  公开（公告）日：2014-08-21

  The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

  本发明提供了一种一锅多酶法，用于从简单糖起始材料制备UDP糖。该发明还提供了一种一锅多酶法，用于从简单糖起始材料制备寡糖。
• Improved one-pot multienzyme (OPME) systems for synthesizing UDP-uronic acids and glucuronides
  作者：Musleh M. Muthana、Jingyao Qu、Mengyang Xue、Timofey Klyuchnik、Alex Siu、Yanhong Li、Lei Zhang、Hai Yu、Lei Li、Peng G. Wang、Xi Chen

  DOI：10.1039/c4cc10306h

  日期：——

  Efficient one-pot multienzyme (OPME) systems were established for the synthesis of UDP-GlcA, UDP-GalA, and glucuronides from simple monosaccharides.

  高效的一锅多酶（OPME）系统已经建立起来，用于从简单单糖合成UDP-GlcA、UDP-GalA和葡萄糖醛酸酯。
• Synthesis ofStreptococcus pneumoniae Type 3 Neoglycoproteins Varying in Oligosaccharide Chain Length, Loading and Carrier Protein
  作者：Dirk J. Lefeber、Johannis P. Kamerling、Johannes F. G. Vliegenthart

  DOI：10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-t

  日期：2001.10.15

  The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (1), beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (2), and beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH4)NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well-defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.
• Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide
  作者：Baolin Wu、Na Wei、Vireak Thon、Mohui Wei、Zaikuan Yu、Yongmei Xu、Xi Chen、Jian Liu、Peng George Wang、Tiehai Li

  DOI：10.1039/c5ob00462d

  日期：——

  A biotinylated heparosan hexasaccharide was synthesized by a facile chemoenzymatic approach in a one-pot multi-enzyme fashion.

  通过一种简便的化学酶法，以一锅多酶的方式合成了生物素化的肝素六糖。
• Tailored Design and Synthesis of Heparan Sulfate Oligosaccharide Analogues Using Sequential One-Pot Multienzyme Systems
  作者：Yi Chen、Yanhong Li、Hai Yu、Go Sugiarto、Vireak Thon、Joel Hwang、Li Ding、Liana Hie、Xi Chen

  DOI：10.1002/anie.201305667

  日期：2013.11.4

  Heparan sulfate analogues: Highly efficient one‐pot multienzyme (OPME) chemoenzymatic systems for the activation and transfer of N‐acetylglucosamine (GlcNAc) and glucuronic acid (GlcA) have been developed. They were applied to the sequential tailored synthesis of N‐sulfated analogues of heparan sulfate oligosaccharides, which could be potential therapeutics.

  硫酸乙酰肝素类似物：已经开发出高效的一锅多酶（OPME）化学酶系统，用于激活和转移N-乙酰氨基葡萄糖（GlcNAc）和葡萄糖醛酸（GlcA）。它们被应用于硫酸乙酰肝素寡糖的N-硫酸化类似物的连续定制合成，这可能是潜在的治疗方法。