(2S,4S)-xylaric acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,4S)-xylaric acid
• 英文别名: arabinaric acid；(2S,4S)-2,3,4-trihydroxypentanedioic acid
• 化学式: C₅H₈O₇
• 分子量: 180.114
• InChiKey: NPTTZSYLTYJCPR-HRFVKAFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S)-xylaric acid 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 28.0h， 生成 N,N'-dimethyl-D-arabinaramide
  参考文献：
  名称：

  Pentaric Acids and Derivatives from Nitric Acid–Oxidized Pentoses

  摘要：

  This report describes the preparation of the four stereoisomeric pentaric acids by nitric acid oxidation of d-xylose, d-arabinose, l-arabinose, and d-ribose, with xylaric, d-arabinaric, and l-arabinaric acids being made in a reactor under computer control. The pentaric acids were converted to their crystalline N,N-dimethylpentaramides, derivatives that proved useful for isolation of the arabinaric acids from their respective oxidation mixtures. The N,N-dimethylpentaramides were readily convertible to the corresponding pentaric acid disodium salts in aqueous sodium chloride. The 2,3,4-O-triacetyl-N,N-dimethylpentaramides of xylaric, l-arabinaric, and ribaric acid were also prepared. Ribaric acid was isolated as crystalline 1,4(5,2)-ribarolactone and further characterized by x-ray crystallography.

  DOI：

  10.1080/07328303.2012.745550
• 作为产物：
  描述：

  阿拉伯糖 在 1 wt% Au/TiO₂ 、 platinum embedded nanoporous carbon 、 氧气 作用下， 以 水 为溶剂， 75.0~100.0 ℃ 、8.38 MPa 条件下， 反应 3636.0h， 生成 (2S,4S)-xylaric acid
  参考文献：
  名称：

  [EN] PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS
  [FR] PROCÉDÉS DE PRÉPARATION D'ACIDES ALDARIQUES, ALDONIQUES ET URONIQUES

  摘要：

  描述了制备阿尔达酸、醛酸、糖醛酸和/或内酯的各种工艺。例如，描述了通过催化氧化C2-C7醛酸和/或内酯以及/或C2-C7醛糖制备C2-C7阿尔达酸和/或内酯的工艺。

  公开号：

  WO2021101810A1

文献信息

• The Formation of Polyhydroxy-dialdehydes. II.<i>d</i>-Lyxo-trihydroxy-glutaric Dialdehyde and its Derivatives
  作者：Koichi Iwadare

  DOI：10.1246/bcsj.16.144

  日期：1941.5

  (1) Monoacetone-d-mannose was now obtained as colourless crystalline needles and its structure was established as 2,3-monoacetone-d-mannofuranose (III). Melting point, 80.5–82°. [α]D15=+4.5° (5 minutes)→−3.7° (40 hours) in water. And triaeetyl-monoacetone-d-mannose was ascertained to have the constitution (VI).(2) Bis-phenylhydrazone of d-lyxo-trihydroxy-glutarie dialdehyde was obtained as colourless needles, starting from 2,3-monoacetone-d-mannofuranose. Melting point, 168.5–169°. [α]D15=−72° in pyridine. Equilbrium rotation of d-lyxo-trihydroxy-glutaric dialdehyde was measured. [α]D15=+5° in water. Bis-p-nitrophenylhydrazone of d-lyxo-trihydroxyglutaric dialdehyde was obtained as orange-yellow leaflets. Melting point, 207–207.5°.Strontium salt of d-lyxo-trihydroxy-glutaric acid was obtained by oxidizing the dialdehyde with bromine in presence of strontium carbonate.

  （1）现在得到了无色的针状晶体单丙酮-d-甘露糖，并确定其结构为2,3-单丙酮-d-甘露呋喃糖（III）。熔点为80.5-82°C。[α]D15=+4.5°（5分钟）→-3.7°（40小时）在水中。三乙酰基-单丙酮-d-甘露糖被确定具有结构（VI）。 （2）从2,3-单丙酮-d-甘露呋喃糖开始，得到了无色的针状晶体d-来索-三羟基戊二酸二醛的双苯腙。熔点为168.5-169°C。[α]D15=-72°在吡啶中。测量了d-来索-三羟基戊二酸二醛的平衡旋转。[α]D15=+5°在水中。得到了橙黄色的d-来索-三羟基戊二酸二醛的双对硝基苯腙，熔点为207-207.5°。通过在碳酸锶存在下用溴氧化二醛，得到了d-来索-三羟基戊二酸的锶盐。
• Haemolysis due to active venous drainage during cardiopulmonary bypass: comparison of two different techniques
  作者：Silvia Cirri、Luca Negri、Marco Babbini、Giorgio Latis、Boutros Khlat、Giuseppe Tarelli、Paolo Panisi、Enzo Mazzaro、Alessandro Bellisario、Bruna Borghetti、Fernanda Bordignon、Mario Ferrara、Helga Pavan、Massimo Meco

  DOI：10.1177/026765910101600408

  日期：2001.7

  To facilitate mini-access for cardiac surgery, two different methods of active venous drainage are used: vacuum assisted drainage and centrifugal pump aspiration on the venous line. The aim of this study was to compare the haemolysis produced using these two techniques.

  From June to December 1999, 50 consecutive patients were operated on using a ministernotomy. All of these patients had valvular surgery for either valve repair or valve replacement (9 MVRepair, 11 MVR, 29 AVR, 1 AVR+MVR). They were randomized into two groups: Group A, 25 patients who underwent surgery where vacuum assisted drainage was used, and Group B, 25 patients where kinetic asssisted venous drainage with centrifugal pump venous aspiration was used. Patient characteristics of both groups were similar for age, gender, body weight, body surface area, height, cardiopulmonary bypass (CPB) time, aortic crossclamp time, priming volume, cardioplegia volume, haemoglobin concentration, haematocrit, serum creatinine, bilirubin, lactate dehydrogenase (LDH), serum glutamic oxaloacetic transaminase (sGOT), serum glutamic pyruvic transaminase (sGPT), aptoglobin, reticulocytes, and platelet count. We checked all these laboratory parameters preoperatively, at the end of CPB, and 2 and 24 h after operation. We also checked haemoglobinuria at these same time points. We assessed blood loss at 6, 12, and 24 h after the operation and calculated total postoperative bleeding. There was a tendency towards a greater increase in LDH, sGOT and sGPT in Group A more than in Group B, but these data did not reach statistical significance. Platelet count was always lower in Group A and aptoglobin increased in Group A more than in Group B. More patients in Group A had haemoglobinuria.

  These findings indicate that haemolysis is increased more in patients treated with vacuum assisted drainage, when compared to the rise in haemolysis in those treated with centrifugal pump venous drainage. Total bleeding is also greater in Group A.

  为了促进心脏手术的微创访问，使用了两种不同的主动静脉引流方法：真空辅助引流和离心泵吸引静脉线。本研究的目的是比较使用这两种技术产生的溶血现象。 从1999年6月到12月，连续50名患者接受了微胸骨切开手术。所有这些患者都接受了瓣膜手术，进行了瓣膜修复或瓣膜置换（9例二尖瓣修复，11例二尖瓣置换，29例主动脉瓣置换，1例主动脉瓣+二尖瓣置换）。他们被随机分为两组：A组，25名接受了使用真空辅助引流的手术的患者，和B组，25名接受了使用离心泵吸引静脉引流的动力学辅助引流的患者。两组患者的特征在年龄、性别、体重、体表面积、身高、体外循环（CPB）时间、主动脉阻断时间、灌注量、心肌保护液量、血红蛋白浓度、红细胞比容、血清肌酐、胆红素、乳酸脱氢酶（LDH）、血清谷草转氨酶（sGOT）、血清谷丙转氨酶（sGPT）、适配蛋白、网织红细胞和血小板计数方面相似。我们在术前、CPB结束时以及术后2小时和24小时检查了所有这些实验室参数。我们还在这些时间点检查了溶血尿。我们评估了术后6、12和24小时的出血量，并计算了总术后出血量。A组中LDH、sGOT和sGPT的增加趋势比B组更明显，但这些数据并未达到统计学意义。血小板计数在A组始终较低，适配蛋白在A组中的增加超过了B组。A组中有更多患者出现溶血尿。 这些发现表明，与使用离心泵静脉引流治疗的患者相比，使用真空辅助引流的患者溶血现象增加更多。总出血量在A组也更大。
• Oxydativer Abbau von Uronsäuren und Derivate der Trioxyglutarsäuren
  作者：E. Hardegger、K. Kreis、D. Spitz

  DOI：10.1002/hlca.19520350336

  日期：1952.5.2

  Die Identifizierung von Aldo-hexuronsäuren anhand von Trioxyglutar- und Zucker- bzw. Schleimsäuren wird ausführlich diskutiert.

  详细讨论了基于三氧戊二酸和糖或粘液酸的醛基己糖醛酸的鉴定。
• The reaction of hyaluronic acid and its monomers, glucuronic acid and N-acetylglucosamine, with reactive oxygen species
  作者：Michael Jahn、John W Baynes、Gerhard Spiteller

  DOI：10.1016/s0008-6215(99)00186-x

  日期：1999.10

  meso-Tartaric acid, arabinuronic acid, arabinaric acid and glucaric acid were identified by GC-MS as oxidation products of glucuronic acid. When GlcNAc was oxidised, erythronic acid, arabinonic acid, 2-acetamido-2-deoxy-gluconic acid, glyceric acid, erythrose and arabinose were formed. NaOCl oxidation of HA yielded meso-tartaric acid; in addition, arabinaric acid and glucaric acid were obtained by

  滑膜液是约0.15％（w / v）的透明质酸（HA）水溶液，透明质酸是由GlcA和GlcNAc的交替单元组成的多糖。在患有类风湿性关节炎的患者的滑液中，HA被认为是由Fenton化学产生的自由基（Fe2 + / H2O2）或由髓过氧化物酶产生的NaOCl所降解。我们研究了这两种反应物在生理缓冲液中与HA以及与相应单体GlcA和GlcNAc的模型反应过程。气相色谱-质谱法鉴定了内消旋-酒石酸，阿拉伯糖醛酸，阿拉伯糖酸和葡糖二酸为葡萄糖醛酸的氧化产物。当氧化GlcNAc时，形成了赤藓酸，阿拉伯糖酸，2-乙酰氨基-2-脱氧葡萄糖酸，甘油酸，赤藓糖和阿拉伯糖。NaOCl氧化HA生成中酒石酸；此外，通过用Fe 2+ / H 2 O 2氧化获得阿拉伯酸和葡糖二酸。这些结果表明HA的氧化降解主要在葡萄糖醛酸残基处进行。介孔-酒石酸可能是透明质酸盐氧化的有用生物标志物，因为它是由NaOCl和Fenton化学产生的。
• Synthesis of aldonolactones, aldarolactones, and aldarodilactones using gas sparging
  申请人：Chenault Keith Henry

  公开号：US20060084817A1

  公开（公告）日：2006-04-20

  Aldaric acids, aldonic acids, and their corresponding salts are cyclized to the corresponding lactone or dilactone using gas sparging to remove water.

  Aldaric酸，醛酸及其相应的盐通过气体冲洗去除水分，环化成相应的内酯或二内酯。