guanosine 5'-monophosphate sodium salt | 3106-17-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: guanosine 5'-monophosphate sodium salt
• 英文别名: Guanine-5'-monophosphate disodium salt；sodium;[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 3106-17-0
• 化学式: C₁₀H₁₃N₅O₈P*Na
• 分子量: 385.205
• InChiKey: ZHZRSXKCIPFRLW-GWTDSMLYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.79
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  guanosine 5'-monophosphate sodium salt 在 1-(benzenesulfonyl)-3-methylimidazolium triflate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.02h， 生成 guanosine 5'-triphosphate triammonium salt
  参考文献：
  名称：

  磺酰基咪唑鎓盐作为快速高效合成核苷多磷酸盐及其缀合物的试剂

  摘要：

  描述了使用磺酰亚胺咪唑鎓盐作为关键试剂合成核苷多磷酸盐及其缀合物的方法。该方法是快速且高产率的，不需要供体或受体的事先保护和随后的脱保护，并且可以用于活化核苷单，二和三磷酸，并且可以使用各种各样的受体和供体。

  DOI：

  10.1021/ol203178k

文献信息

• A multi-centered electrophile formed from a unique bioactive cyclic hydroxamic acid, 4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
  作者：Yuichi Hashimoto、Takayoshi Ishizaki、Koichi Shudo

  DOI：10.1016/s0040-4020(01)96098-3

  日期：1991.3

  4-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (HMBOA) is a compound of considerable interest because of its pharmacological, agrochemical, and antimicrobial properties. A plausible bioactive metabolite of HMBOA is 4-acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (AMBOA). Electrophilic reactions of AMBOA with phenols, anilines, thiols, heteroaromatics, amino acid derivatives and nucleic acids were investigated in relation

  4-羟基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-1（HMBOA）由于其药理，农药和抗微生物特性而备受关注。HMBOA的可能的生物活性代谢物是4-乙酰氧基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-one（AMBOA）。研究了AMBOA与苯酚，苯胺，硫醇，杂芳族化合物，氨基酸衍生物和核酸的亲电反应，以及该化合物引起的生物学效应的化学机理。结果表明，HMBOA在代谢O-酰化后充当蛋白质和核酸的烷基化剂。
• Substitution of inosine and guanosine 5′-monophosphate for chloride, and water on PdII(polyaminopolycarboxylate) complexes: mechanistic controls in forming PdII(pac)L or PdII(pac)L2 products
  作者：Thomas W Stringfield、Rex E Shepherd

  DOI：10.1016/s0020-1693(00)00238-3

  日期：2000.11

  such that the final coordination of inosine is favored at the N-7 donor site. The structure of the product was deduced from 1H and 13C NMR studies. These [Pd(pac)L] products are consistent with a common trigonal bipyramidal intermediate with the entering Ino group displacing an in-plane glycinato group. Substitution of one Ino on [PdII(mida)Cl]− results in both glycinato donors being made pendant.

  用[Pd II（pac）（D 2 O）]复合物（pac =带有pac = mida 2-的聚氨基聚羧酸盐）和[Pd 2  II（pac）（D 2 O）2 ]（pac ）取代一个肌苷（Ino）= HDTA 4-和EGTA 4-其中进入伊诺配体驻留生产产品反式到亚氨基二乙酸ñ供体和亚氨基二乙酸供体的2个glycinato臂具有一个“上，和一个断开”布置。反应是在执行pD范围为5.0–6.0，以确保在起始[Pd（pac）（D 2O）]复杂，其范围应使N-7供体位点的肌苷达到最终配位。产物的结构由1 H和13 C NMR研究推论得出。这些[Pd（pac）L]产物与常见的三角双锥体中间体一致，进入的Ino基团取代了平面内的甘氨酸基团。在[Pd II（mida）Cl] -上取代一个Ino会导致两个甘氨酸供体被悬垂。一个不同的，更方形的金字塔形中间体会生成此产品，而TBP几何图形则不会。形成稳定的bis
• Efficient synthesis of cytidine diphosphate diacylglycerol: A crucial precursor of glycerophospholipids biosynthesis
  作者：Yuki Kitaura、Rina Ueshima、Kanae Sano、Takashi Kikuma、Yoichi Takeda

  DOI：10.1016/j.tetlet.2023.154781

  日期：2023.11

  glycerophospholipids comprising lipid membranes. However, achieving efficient condensation of phosphatidic acid with cytidine monophosphate (CMP) in the chemical synthesis of CDP-DAG remains challenging. This study demonstrated the efficient synthesis of liponucleotides using sulfonyl imidazolium triflate as an activator. The pyridinium salts of CMP and phosphatidic acid were rapidly activated with sulfonylimidazolium

  胞苷二磷酸二酰基甘油 (CDP-DAG) 是形成多种构成脂质膜的甘油磷脂的重要前体。然而，在 CDP-DAG 的化学合成中实现磷脂酸与胞苷单磷酸 (CMP) 的有效缩合仍然具有挑战性。这项研究证明了使用磺酰咪唑鎓三氟甲磺酸盐作为活化剂可以有效合成脂核苷酸。这CMP 和磷脂酸的吡啶鎓盐被磺酰咪唑鎓盐快速活化，以高产率产生 CDP-DAG。因此，磺酰咪唑鎓盐是合成CDP-DAG的有用活化剂。这种方法有助于开发重要工具来阐明甘油磷脂（细胞膜的重要成分）的生物合成和调节机制。这项研究为脂核苷酸（例如 CDP-DAG）的合成及其在理解细胞膜形成方面的重要性提供了宝贵的见解。
• Purygin, P. P., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1713 - 1715
  作者：Purygin, P. P.

  DOI：——

  日期：——
• Characterization of Complexes of Nucleoside-5′-Phosphorothioate Analogues with Zinc Ions
  作者：Alon Haim Sayer、Yehudit Itzhakov、Noa Stern、Yael Nadel、Bilha Fischer

  DOI：10.1021/ic400878k

  日期：2013.10.7

  On the basis of the high affinity of Zn2+ to sulfur and imidazole, we targeted nucleotides such as GDP-beta-S, ADP-beta-S, and AP(3)(beta-S)A, as potential biocompatible Zn2+-chelators. The thiophosphate moiety enhanced the stability of the Zn2+-nucleotide complex by about 0.7 log units. ATP-alpha,beta-CH2-gamma-S formed the most stable Zn2+-complex studied here, log K 6.50, being similar to 0.8 and similar to 1.1 log units more stable than ATP-gamma-S-Zn2+ and ATP-Zn2+ complexes, and was the major species, 84%, under physiological pH. Guanine nucleotides Zn2+ complexes were more stable by 0.3-0.4 log units than the corresponding adenine nucleotide complexes. Likewise, AP(3)(beta-S)A-zinc complex was similar to 0.5 log units more stable than AP(3)A complex. H-1- and P-31 NMR monitored Zn2+ titration showed that Zn2+ coordinates with the purine nucleotide N7-nitrogen atom, the terminal phosphate, and the adjacent phosphate. In conclusion, replacement of a terminal phosphate by a thiophosphate group resulted in decrease of the acidity of the phosphate moiety by approximately one log unit, and increase of stability of Zn2+-complexes of the latter analogues by up to 0.7 log units. A terminal phosphorothioate contributed more to the stability of nucleotide-Zn2+ complexes than a bridging phosphorothioate.