sodium D-glucuronate | 24016-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium D-glucuronate
• 英文别名: sodium D-glucopyranuronate；sodium;(2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• CAS: 24016-65-7
• 化学式: C₆H₉O₇*Na
• 分子量: 216.123
• InChiKey: MSXHSNHNTORCAW-KZUGWDFCSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -7.46
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium D-glucuronate 在 高氯酸,吡啶 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 15.0h， 生成 sodium 1-deoxy-1-(N-hydroxy-4-phenoxyanilino)-β-D-glucopyranuronate
  参考文献：
  名称：

  Yoshioka, Tadao; Yamada, Hidetoshi; Uematsu, Takayoshi, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1271 - 1276

  摘要：

  DOI：
• 作为产物：
  描述：

  O1,O2-isopropylidene-β-L-idofuranuronic acid ; calcium salt 在 KU-2 cation exchange resin 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以52%的产率得到sodium D-glucuronate
  参考文献：
  名称：

  EP1500660

  摘要：

  公开号：

文献信息

• Synthesis, characterization, and conformation in solution of a novel d-glucurono-6,1-lactam derivative
  作者：Yasuko Takeda、Toshio Akimoto、Yoshimasa Kyogoku

  DOI：10.1016/s0008-6215(00)81072-1

  日期：1982.8

  6-lactam ( 2 ), a novel d -glucorono-6,1-lactam derivative. Its conformation in solution, examined by 1 H- and 13 C-n.m.r. and compared with the crystal structure, corresponds to a fairly rigid ring system, the pyranose ring adopting a near B O,3 ( d ) boat form in solution and a distorted 1 C 4 ( d ) chair conformation in the crystalline state. The closely related 2,3,4-tri- O -acetyl-β- d -glucopyranurono-6

  摘要在吡啶存在下，于室温下用乙酸酐将2'-（β-d-葡萄糖基吡喃葡萄糖基尿酸酯钠）异烟酰肼在室温下延长处理约110小时，得到2,3,4-三-O-乙酰基-N-（二乙酰氨基）- β-d-葡萄糖吡喃并-1,6-内酰胺（2），一种新的d-葡萄糖基-6,1-内酰胺衍生物。由1 H-和13 Cn.mr检查并在溶液中的构象，并与晶体结构进行比较，它对应于一个相当刚性的环系统，吡喃糖环在溶液中采用接近BO，3（d）的船形，并扭曲了1 C 4（d）椅构型呈结晶态。密切相关的2,3,4-tri-O-乙酰基-β-d-吡喃葡萄糖醛-6,1-内酯（4）和2,3,4-tri-O-乙酰基-1,6-脱水-β- d-葡萄糖（3）呈扭曲的1 C 4（d）构象，呈溶液形式和晶体形式。根据4的晶体结构数据，
• Synthesis and Enzymatic Evaluation of Substrates and Inhibitors of ?-Glucuronidases
  作者：Roland Hoos、Jiang Huixin、Andrea Vasella、Patrick Weiss

  DOI：10.1002/hlca.19960790703

  日期：1996.10.30

  4-methylumbelliferyl β-D-glucuronide (=(4-methyl-2-oxo-2H-1-benzopyran-7-yl β-D-glucopyranosid)uronic acid; 6) were synthesized and evaluated as substrates of β-glucuronidases. Similarly, the phenylcarbamate 7 and its phosphono analogue 8 were prepared and evaluated as inhibitors. To examine the diastereoselectivity of the phosphorylation, we also synthesized the protected L-ido-D-gluco-, and D-galacto-configurated

  4-甲基伞形基β-D-葡糖醛酸（=（4-甲基-2-氧代-2 H -1-苯并吡喃-7-基β-D-吡喃葡糖苷）糖醛酸的膦酰基和四唑基类似物4和5 ; 6）合成并评估为β-葡萄糖醛酸苷酶的底物。类似地，制备氨基甲酸苯酯7及其膦酰基类似物8，并将其评估为抑制剂。为了检查磷酸化的非对映选择性，我们还合成受保护的L- IDO -D-葡糖- ，和D-半乳-构型磷glycopyranuronates 12，图13，21，22，34和35。遵循了两种策略。在第一个中，将葡糖醛酸19脱羧至11，并通过20进一步转化成三氯乙亚氨酸酯10（方案2）。用（MeO）3 P磷酸化10生成非对映异构体12和13，其非对映选择性取决于溶剂。在MeCN中，以1：1的比例获得12和13，而在非参与溶剂中，L- ido 12是主要的非对映异构体。乙酸盐11对（MeO）是惰性的3 P，但与（PhO）3 P反应生成异头混合物21/22，同时在中间体the盐中保持稳定的1
• Self-immolative magnetic resonance imaging contrast agents sensitive to beta-glucuronidase
  申请人：Duimstra A. Joseph

  公开号：US20060088475A1

  公开（公告）日：2006-04-27

  The present invention relates to magnetic resonance imaging (MRI) contrast agent. In particular, the present invention provides MRI contrast agents that are sensitive to the enzyme beta-glucoronidase. The MRI contrast agents provide compositions and methods for non-invasive diagnostic imaging of tissues, including necrotic tumors.

  本发明涉及磁共振成像（MRI）造影剂。具体而言，本发明提供对酶β-葡萄糖醛酸酶敏感的MRI造影剂。MRI造影剂提供了用于非侵入性诊断组织，包括坏死肿瘤的成分和方法。
• NMR and MS study of the formation of β-<scp>d</scp>-glucopyranosylamine uronic acid in aqueous solution
  作者：Ali Ghadban、Luca Albertin、Eric Condamine、Rédéo W. Moussavou Mounguengui、Alain Heyraud

  DOI：10.1139/v11-064

  日期：2011.8

  The products of the reaction of d-glucuronic acid with various combinations of ammonia and volatile ammonium salts in water were studied by NMR and MS spectroscopy. For long reaction times (~24 h), the expected products β-d-glucopyranosylamine uronic acid and ammonium N-(β-d-glucopyranosyluronic acid)carbamate were obtained in good-to-high yield, whereas seven intermediate species were identified in samples taken at earlier reaction times. ¹H–¹H homonuclear and ¹H–¹³C heteronuclear correlation experiments enabled a complete assignment of the ¹H and ¹³C NMR spectra of the starting and final compounds, and a partial assignment of the peaks of intermediate species. Based on these results, a ¹H NMR protocol for the quantification of the different compounds taking part in the reaction was developed, which was used to monitor the evolution of the composition of an early reaction sample redissolved in D₂O. It was thus established that two of the observed intermediate species are actually the α anomer of the main products, whereas the others are precursors to the formation of α/β-d-glucopyranosylamine uronic acid and ammonium N-(α/β-d-glucopyranosyluronic acid)carbamate. The correct assignments for the ¹H and ¹³C spectra of d-glucuronic acid in D₂O are also reported.

  该研究使用核磁共振（NMR）和质谱（MS）光谱研究了d-葡萄糖醛酸与氨和挥发性铵盐在水中反应产物。在长时间反应（约24小时）中，预期产物β-d-葡萄糖吡喃氨基葡糖醛酸和铵盐N-(β-d-葡糖吡喃醛酸)氨基甲酸酯以较高产率得到，而在较早反应时间采集的样品中鉴定了七种中间产物。通过1H-1H同核和1H-13C异核相关实验，完成了起始和最终化合物的1H和13C NMR光谱的完整分配，并对中间产物的峰进行了部分分配。基于这些结果，开发了用于定量参与反应的不同化合物的1H NMR协议，用于监测在D2O中重新溶解的早期反应样品的组成演变。因此确定了观察到的两种中间产物实际上是主要产物的α异构体，而其他产物是α/β-d-葡糖吡喃氨基葡糖醛酸和铵盐N-(α/β-d-葡糖吡喃醛酸)氨基甲酸酯的前体。还报告了在D2O中d-葡糖醛酸的1H和13C光谱的正确分配。
• Bioconjugation of D-glucuronic acid sodium salt to well-defined primary amine-containing homopolymers and block copolymers
  作者：Alp H. Alidedeoglu、Adam W. York、Dale A. Rosado、Charles L. McCormick、Sarah E. Morgan

  DOI：10.1002/pola.24083

  日期：——

  as the chain transfer agent and 4,4′‐azobis(4‐cyanovaleric acid) (V‐501) as the initiator at 70 °C. The resulting well‐defined PAPMA was then conjugated with D‐glucuronic acid sodium salt through reductive amination in alkaline medium (pH 8.5) at 45 °C. The successful bioconjugation was proven through proton (1H) and carbon (13C) nuclear magnetic resonance spectroscopy and matrix‐assisted laser desorption/ionization

  演示了通过在水性介质中对水溶性水溶性伯胺甲基丙烯酰胺聚（N- [3-氨基丙基]甲基丙烯酰胺）（PAPMA）进行一步后聚合修饰而制备的，定义明确的羧酸官能化糖聚合物。PAPMA首先通过水性可逆加成-断裂链转移聚合在水性缓冲液中进行聚合，使用4-氰基戊酸二硫代苯甲酸酯作为链转移剂，并以4,4'-偶氮双（4-氰基戊酸）（V-501）作为引发剂，温度为70 ℃。然后，通过在碱性介质（pH 8.5）中于45°C进行还原胺化，将得到的定义明确的PAPMA与D-葡萄糖醛酸钠盐偶联。通过质子（1 H）和碳（13C）核磁共振波谱和基质辅助激光解吸/电离飞行时间质谱分析，表明接近定量转换。类似的生物缀合反应用的聚（2-氨乙基甲基丙烯酸酯）（PAEMA）和聚（2-氨乙基甲基丙烯酸酯进行b -聚（ñ - [2-羟基丙基]甲基丙烯酰胺）（PAEMA- b。-PHPMA）对于PAEMA均聚物但是，嵌段共聚物和嵌段共聚