(2S,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-甲醛 | 3110-98-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: (2S,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-甲醛
• 中文别名: 2H-1-苯并吡喃-2-酮,5-羟基-6-甲氧基-4-甲基-
• 英文名称: Adenosin-5'-aldehyd
• 英文别名: (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carbaldehyde
• CAS: 3110-98-3
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: CWNMDMYGRVHXDR-KQYNXXCUSA-N

物化性质

• 沸点：
  668.7±65.0 °C(Predicted)
• 密度：
  2.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-甲醛 、 水 、 氧气 生成 Adenin-9-yl riburonosate(1-) 、 氢(+1)阳离子 、 双氧水
  参考文献：
  名称：

  核苷氧化酶，一种过氧化氢形成性氧化酶，来自脑膜炎黄杆菌。

  摘要：

  从脑膜炎黄杆菌T-2799中纯化出一种能够催化核苷氧化为5（prm1）-羧酸核苷形成过氧化氢的新型酶。该酶的分子量约为500,000，在十二烷基硫酸钠-聚丙烯酰胺凝胶电泳中检测到四个不同的亚基（分子量分别为81,000、69,000、33,000和16,000）。根据纯化酶的可见吸收光谱，该酶被认为是血红蛋白。它还包含共价结合的黄素腺嘌呤二核苷酸。各种核苷，例如腺苷（K（infm）= 48μM），肌苷（K（infm）= 66μM），鸟苷（K（infm）= 21μM），胸苷（该酶将K（infm）= 50μM，尿苷（K（infm）= 80μM）和胞苷（K（infm）= 50μM）氧化，但核苷酸

  DOI：

  10.1128/aem.63.11.4282-4286.1997
• 作为产物：
  描述：

  N⁶-benzoyl-5'-deoxy-2',3'-O-isopropylidiene-5',5'-(N,N'-diphenylethylenediamino)adenosine 在 ammonium hydroxide 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.33h， 生成 (2S,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-甲醛
  参考文献：
  名称：

  腺苷5'-甲醛：S-腺苷-L-高半胱氨酸水解酶的有效抑制剂。

  摘要：

  合成了5'-腺苷腺苷（3）及其4'-末端（4），它们是重组大鼠肝脏AdoHcy水解酶的有效的基于I型机理的抑制剂，k2 / KI值为16.7 x 10（-3）和5.5 x 10（-3）nM-1 min-1。3和4是有效的AdoHcy水解酶抑制剂的观察结果支持以下假设：它们在（Z）-和（E）-4'，5'-didehydro-5'-deoxy-5机理中起关键中间体的作用'-氟腺苷1和2使该酶失活。

  DOI：

  10.1021/jm00059a013

文献信息

• Anticancer and Antiviral Effects and Inactivation of <i>S</i>-Adenosyl-<scp>l</scp>-homocysteine Hydrolase with 5‘-Carboxaldehydes and Oximes Synthesized from Adenosine and Sugar-Modified Analogues
  作者：Stanislaw F. Wnuk、Chong-Sheng Yuan、Ronald T. Borchardt、Jan Balzarini、Erik De Clercq、Morris J. Robins

  DOI：10.1021/jm960828p

  日期：1997.5.1

  5'-carboxaldehyde analogues by Moffatt oxidation (dimethyl sulfoxide/dicyclohexylcarbodiimide/dichloroacetic acid) or with the Dess-Martin periodinane reagent. Hydrolysis of a 5'-fluoro-5'-S-methyl-5'-thio (alpha-fluoro thioether) arabinosyl derivative also gave the 5'-carboxaldehyde. Treatment of 5'-carboxaldehydes with hydroxylamine [or O-(methyl, ethyl, and benzyl)hydroxylamine] hydrochloride gave

  通过Moffatt氧化（二甲基亚砜/二环己基碳二亚胺/二氯乙酸）或用Dess-Martin高碘烷试剂将选择性保护的腺嘌呤核苷转化为5'-甲醛醛类似物。5'-氟-5'-S-甲基-5'-硫代（α-氟硫醚）阿拉伯糖基衍生物的水解也得到5'-甲醛。用羟胺[或O-（甲基，乙基和苄基）羟胺]盐酸盐处理5'-甲醛，得到E / Z肟。用三氟乙酸水溶液和丙酮处理纯化的肟可实现反式肟化反应，从而提供干净的5'-甲醛样品。腺苷（Ado）-5'-甲醛及其4'-末端是S-腺苷-L-高半胱氨酸（AdoHcy）水解酶的有效抑制剂。它们与酶有效结合并在C3'处发生氧化 得到3'-酮类似物，同时降低NAD +辅因子，得到无活性的，紧密结合的NADH-酶复合物（I型辅因子耗竭抑制）。用含有核糖顺式2'，3'-乙二醇的5'-羧醛观察到了有效的I型抑制作用。它们的肟衍生物是“前抑制剂”，它们经过酶催化水解后在活性位点释放抑制剂。
• Synthesis and Characterization of 3‘,4‘-Anhydroadenosylcobalamin:  A Coenzyme B₁₂ Analogue with Unusual Properties
  作者：Olafur Th. Magnusson、Perry A. Frey

  DOI：10.1021/ja0013780

  日期：2000.9.1

  The question of how coenzyme B-12-dependent enzymes facilitate the cleavage of the Co-C bond of the cofactor is of interest. We have synthesized an analogue of 5'-deoxyadenosylcobalamin (AdoCbl(1)) designed to stabilize the 5'-deoxyadenosyl radical (5'-deoxyadenosine-5'-yl) that is produced upon homolysis of the Co-C bond. By replacement of the upper axial ligand of AdoCbl by a 3',4'-anhydro-5'-deoxyadenosyl moiety, the radical formed on the nucleoside analogue is stabilized by allylic delocalization. The compound, 5'-deoxy- 3',4'-anhydroadenosylcobalamin (3',4'-anAdoCbl) was synthesized by chemical and enzymatic methods. The final step was coupling of cob(I)alamin and 3',4'-anhydroATP catalyzed by CobA, an ATP: corrinoid adenosyltransferase. 3',4'-anAdoCbl displays interesting properties. The compound has not been purified to homogeneity due to its thermal and oxygen sensitivity. It was characterized by UV-vis spectroscopy, ESI-MS, and NMR spectroscopy. The bond dissociation energy of the Co-C bond of the analogue was measured by radical trapping techniques. A significantly weaker bond (24 +/- 2 kcal/mol) as compared to AdoCbl (30 kcal/mol) was observed, as was homolytic cleavage at ambient temperature. Photolysis experiments conducted under anaereobic conditions reveal no formation of cob(II)alamin, whereas the compound breaks down rapidly under aerobic conditions as measured by cob(In)alamin formation. We postulate that the weak Co-C bond is cleaved reversibly by photolysis, where recombination of the allylic radical and cob(II)alamin occurs efficiently in the absence of a radical scavanger. Activation of the coenzyme Bit-dependent enzymes diol dehydrase and ethanolamine ammonia-lyase was observed with the cofactor analogue. The measured activity was low and no formation of cob(II)alamin could be detected in the steady-state of the reaction for either enzyme. Comparative interactions of AdoCbl and 3',4'-anAdoCbl with diol dehydrase and ethanolamine ammonia-lyase suggest that cleavage of the Co-C bond is facilitated by enzyme-coenzyme binding contacts that are remote from the Co-C bond.
• METHODS OF DIAGNOSING DISEASE
  申请人：4D Pharma Cork Limited

  公开号：EP3947743A1

  公开（公告）日：2022-02-09
• BIOSENSOR FOR MEASUREMENT OF SPECIES IN A BODY FLUID
  申请人：Nagale P. Milind

  公开号：US20070281321A1

  公开（公告）日：2007-12-06

  Certain embodiments disclosed herein are directed to devices configured to detect the level of a biomarker in a body fluid. In some examples, the device includes two or more electrodes for electrochemical detection of the biomarker in the body fluid. Methods of using the device are also disclosed.
• [EN] BIOSENSOR FOR MEASUREMENT OF SPECIES IN A BODY FLUID<br/>[FR] BIOCAPTEUR POUR LA MESURE D'ESPÈCES DANS UN FLUIDE CORPOREL
  申请人：ESA BIOSCIENCES INC

  公开号：WO2008027098A2

  公开（公告）日：2008-03-06

  [EN] Certain embodiments disclosed herein are directed to devices configured to detect the level of a biomarker in a body fluid. In some examples, the device includes two or more electrodes for electrochemical detection of the biomarker in the body fluid. Methods of using the device are also disclosed.
  [FR] Certains modes de réalisation selon l'invention concernent des dispositifs configurés pour détecter le niveau d'un biomarqueur dans un fluide corporel. Dans certains exemples, le dispositif comprend deux électrodes ou plus pour la détection électrochimique du biomarqueur dans le fluide corporel. L'invention concerne également des procédés d'utilisation du dispositif.