N²-carboxymethylguanosine | 4552-63-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N²-carboxymethylguanosine
• 英文别名: N(2)-carboxymethylguanosine；2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]amino]acetic acid
• CAS: 4552-63-0
• 化学式: C₁₂H₁₅N₅O₇
• 分子量: 341.28
• InChiKey: YSAOPASVXKYEFD-TZQXKBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  179
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-葡萄糖 、 鸟苷 在 氧气 作用下， 以 various solvent(s) 为溶剂， 反应 576.0h， 生成 N²-carboxymethylguanosine
  参考文献：
  名称：

  Reaction of guanosine with glucose under oxidative conditions

  摘要：

  Incubation of glucose with guanosine under oxidative conditions at 37 degrees C or 70 degrees C leads to the formation of a main product, which can be detected by HPLC/DAD, The compound was isolated and identified as N-2-carboxymethyl-guanosine (CMG). To confirm the structure, CMG was also synthesized from glyoxal and guanosine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00343-6

文献信息

• Reactions of 9-substituted guanines with bromomalondialdehyde in aqueous solution predominantly yield glyoxal-derived adducts
  作者：Anne-Mari Ruohola、Niangoran Koissi、Sanna Andersson、Ilona Lepistö、Kari Neuvonen、Satu Mikkola、Harri Lönnberg

  DOI：10.1039/b405117c

  日期：——

  Reactions of 9-ethylguanine, 2′-deoxyguanosine and guanosine with bromomalondialdehyde in aqueous buffers over a wide pH-range were studied. The main products were isolated and characterized by 1H and 13C NMR and mass spectroscopy. The final products formed under acidic and basic conditions were different, but they shared the common feature of being derived from glyoxal. Among the 1 : 1 adducts, 1,N2-(trans-1,2-dihydroxyethano)guanine adduct (6) predominated at pH < 6 and N2-carboxymethylguanine adduct (10a,b) at pH > 7. In addition to these, an N2-(4,5-dihydroxy-1,3-dioxolan-2-yl)methylene adduct (11a,b) and an N2-carboxymethyl-1,N2-(trans-1,2-dihydroxyethano)guanine adduct (12) were obtained at pH 10. The results of kinetic experiments suggest that bromomalondialdehyde is significantly decomposed to formic acid and glycolaldehyde under the conditions required to obtain guanine adducts. Glycolaldehyde is oxidized to glyoxal, which then modifies the guanine base more readily than bromomalondialdehyde. Besides the glyoxal-derived adducts, 1,N2-ethenoguanine (5a–c) and N2,3-ethenoguanine adducts (4a–c) were formed as minor products, and a transient accumulation of two unstable intermediates, tentatively identified as 1,N2-(1,2,2,3-tetrahydroxypropano) (8) and 1,N2-(2-formyl-1,2,3-trihydroxypropano) (9) adducts, was observed.

  研究了 9-乙基鸟嘌呤、2'-脱氧鸟苷和鸟苷与溴丙二醛在水性缓冲液中在宽 pH 范围内的反应。主要产物通过1H和13C NMR和质谱进行分离和表征。在酸性和碱性条件下形成的最终产物不同，但它们具有共同的特征，即衍生自乙二醛。在 1:1 加合物中，pH < 6 时主要为 1,N2-(反式-1,2-二羟基乙醇)鸟嘌呤加合物 (6)，pH > 7 时主要为 N2-羧甲基鸟嘌呤加合物 (10a,b)。 N2-(4,5-二羟基-1,3-二氧戊环-2-基)亚甲基加合物 (11a,b) 和 N2-羧甲基-1,N2-(反式-1,2-二羟基乙醇)鸟嘌呤加合物 (12 ）在pH 10下获得。动力学实验结果表明，在获得鸟嘌呤加合物所需的条件下，溴丙二醛显着分解为甲酸和乙醇醛。乙醇醛被氧化成乙二醛，然后乙二醛比溴丙二醛更容易修饰鸟嘌呤碱基。除了乙二醛衍生的加合物外，还形成了次要产物 1,N2-乙烯基鸟嘌呤 (5a–c) 和 N2,3-乙烯基鸟嘌呤加合物 (4a–c)，以及两种不稳定中间体的短暂积累，初步鉴定为 1,N2 -(1,2,2,3-四羟基丙酸) (8)和1,N2-(2-甲酰基-1,2,3-三羟基丙酸) (9)观察到加合物。
• ARTIFICIAL KIDNEY
  申请人：Relitech B.V.

  公开号：EP2157985A1

  公开（公告）日：2010-03-03
• [EN] ARTIFICIAL KIDNEY<br/>[FR] REIN ARTIFICIEL
  申请人：RELITECH

  公开号：WO2008153396A1

  公开（公告）日：2008-12-18

  [EN] Artificial kidney for gradual, and at least semi-continuous, blood treatment, wherein a blood stream is fed from a body of a living human or animal being into the artificial kidney, where anticoagulation is first effected, blood cells and molecules of large and medium molecular weight, such as proteins, are then primarily separated from plasma and fed back to the blood stream, regulating a water and salt balance by diverting excess plasma water and further removing from the blood stream, plasma or plasma water accumulated and toxic substances, by removal of specific electrolytes and waste products and wherein purified or partially purified plasma and plasma water is being carried back to the blood tract of the body.
  [FR] La présente invention concerne un rein artificiel destiné à un traitement sanguin progressif et au moins semi-continu, dans lequel on alimente un flux sanguin d'un corps d'humain ou d'animal vivant vers le rein artificiel, dans lequel on effectue d'abord une anticoagulation, puis on sépare du plasma principalement des cellules sanguines et des molécules de poids moléculaire élevé et moyen, telles des protéines, et on réintroduit celles-ci dans le flux sanguin, on régule l'équilibre entre l'eau et le sel par la déviation du surplus de liquide plasmatique puis le retrait du flux sanguin du plasma ou liquide plasmatique et des substances toxiques qui se sont accumulées, on retire des électrolytes et des déchets spécifiques, et dans lequel le plasma et le liquide plasmatique purifiés ou partiellement purifiés sont réintroduits dans le système sanguin du corps.