2-Azidoethyl β-D-glucopyranosiduronic acid | 128095-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Azidoethyl β-D-glucopyranosiduronic acid
• 英文别名: 2-Azidoethyl beta-D-glucopyranosiduronic acid；(2S,3S,4S,5R,6R)-6-(2-azidoethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 128095-64-7
• 化学式: C₈H₁₃N₃O₇
• 分子量: 263.207
• InChiKey: XKBPWIGGTKHFLB-UQGZVRACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  2-Azidoethyl β-D-glucopyranosiduronic acid 在 palladium on activated charcoal sodium hydroxide 、 Dowex 1-X₈ (hco3^-) resin 、 氢气 、 溶剂黄146 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.75h， 生成 Nα-(2-Acrylamidoethyl β-D-glucopyranosiduronoyl)-L-lysine
  参考文献：
  名称：

  Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglyco- conjugates therefrom

  摘要：

  Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised. N(epsilon)-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and beta-D-GlcpNAc-(1 --> 3)-beta-D-GlcpA. Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.

  DOI：

  10.1016/s0008-6215(00)90501-9
• 作为产物：
  描述：

  methyl (2-azidoethyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-Azidoethyl β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  从大肠杆菌O6：K54：H10合成与荚膜抗原K54有关的碳水化合物-氨基酸缀合物，并从中合成人工抗原。

  摘要：

  带有酰胺连接的L-丝氨酸的二糖α-L-Rhap-（1 ---- 3）-β-D-GlcpA和β-D-GlcpA-（1 ---- 3）-α-L-Rhap已经合成了代表来自大肠杆菌O6：K54：H10的荚膜多糖的重复单元的L-或苏氨酸。将O-叔丁基保护的氨基酸叔丁酯与相应的生物糖醛酸缩合为2-丙烯酰胺基乙基或2-叠氮基乙基糖苷。通过催化氢化然后进行N-丙烯酰化，叠氮基官能团被丙烯酰胺基取代。通过用三氟乙酸处理除去叔丁基，得到目标单体，将其与丙烯酰胺共聚，得到新的糖缀合物，其可用于免疫化学研究。

  DOI：

  10.1016/0008-6215(92)84175-r

文献信息

• Conjugates containing hydrophilic spacer linkers
  申请人：Leamon Christopher Paul

  公开号：US09138484B2

  公开（公告）日：2015-09-22

  Described herein are compositions and methods for use in targeted drug delivery using cell receptor binding drug delivery conjugates containing hydrophilic spacer linkers for use in imaging, diagnosing, and/or treating diseases and disease states caused by pathogenic cell populations.

  本文件描述了用于靶向药物递送的组合物和方法，使用含有亲水性间隔连接子的细胞受体结合药物递送偶联物，用于成像、诊断和/或治疗由病原性细胞群体引起的疾病和疾病状态。
• CHERNYAK, A. YA.;KONONOV, L. O.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 15,(1989) N0, S. 1394-1410
  作者：CHERNYAK, A. YA.、KONONOV, L. O.、KOCHETKOV, N. K.

  DOI：——

  日期：——
• [EN] ENDOSOMAL CLEAVABLE HYDROPHILIC-MASKED CATIONIC CHARGE DELIVERY VEHICLES<br/>[FR] VÉHICULES ENDOSOMAUX CLIVABLES DE DISTRIBUTION DE CHARGE CATIONIQUE À MASQUAGE HYDROPHILE
  申请人：[en]THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：WO2023168338A2

  公开（公告）日：2023-09-07

  The disclosure provides for compounds and compositions comprising hydrophilicmasked cationic charge dendrimers, and applications thereof, including delivering siRNA, ASO, PMO, PNA, oligonucleotide and nucleic acid vectors. The methods and approaches disclosed herein can also be applied to lipids to make hydrophilic-masked cationic charge lipid nanoparticles for mRNA, RNA, siRNA, DNA, ASO, PMO, PNA, oligonucleotide and nucleic acid vector delivery.
• Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglyco- conjugates therefrom
  作者：Anatoly Ya. Chernyak、Leonid O. Kononov、Palakodety Radha Krishna、Nikolay K. Kochetkov、Alla V. Rama Rao

  DOI：10.1016/s0008-6215(00)90501-9

  日期：1992.3

  Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised. N(epsilon)-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and beta-D-GlcpNAc-(1 --> 3)-beta-D-GlcpA. Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.
• Synthesis of carbohydrate-amino acid conjugates related to the capsular antigen K54 from Escherichia coli O6:K54:H10 and artificial antigens therefrom
  作者：Anatoly Ya. Chernyak、Leonid O. Kononov、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(92)84175-r

  日期：1992.9

  alpha-L-Rhap-(1----3)-beta-D-GlcpA and beta-D-GlcpA-(1----3)-alpha-L-Rhap bearing amide-linked L-serine or L-threonine, which represent the repeating unit(s) of the capsular polysaccharide from E. coli O6:K54:H10, have been synthesised. O-tert-Butyl-protected amino acid tert-butyl esters were condensed with the corresponding biouronic acid as the 2-acrylamidoethyl or 2-azidoethyl glycosides. The azido function was

  带有酰胺连接的L-丝氨酸的二糖α-L-Rhap-（1 ---- 3）-β-D-GlcpA和β-D-GlcpA-（1 ---- 3）-α-L-Rhap已经合成了代表来自大肠杆菌O6：K54：H10的荚膜多糖的重复单元的L-或苏氨酸。将O-叔丁基保护的氨基酸叔丁酯与相应的生物糖醛酸缩合为2-丙烯酰胺基乙基或2-叠氮基乙基糖苷。通过催化氢化然后进行N-丙烯酰化，叠氮基官能团被丙烯酰胺基取代。通过用三氟乙酸处理除去叔丁基，得到目标单体，将其与丙烯酰胺共聚，得到新的糖缀合物，其可用于免疫化学研究。