2',3',4',5'-tetra-O-acetyl-5-deazariboflavin | 59389-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2',3',4',5'-tetra-O-acetyl-5-deazariboflavin
• 英文别名: 5-deaza-(tetra-acetyl)-riboflavin；tetraacetyl 5-deazariboflavin；[(2R,3S,4S)-2,3,4-triacetyloxy-5-(7,8-dimethyl-2,4-dioxopyrimido[4,5-b]quinolin-10-yl)pentyl] acetate
• CAS: 59389-72-9
• 化学式: C₂₆H₂₉N₃O₁₀
• 分子量: 543.53
• InChiKey: OYOLNUGKPCHUAB-ZRBLBEILSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',3',4',5'-tetra-O-acetyl-5-deazariboflavin 在 氨 作用下， 以 甲醇 为溶剂， 反应 19.0h， 以76%的产率得到5-脱氮核黄素
  参考文献：
  名称：

  结构修饰黄素化合物的合成及电化学性质

  摘要：

  已经合成了四种结构改性的黄素化合物，并通过用连二亚硫酸钠化学还原来表征它们的氧化还原电位。除了先前报道的 1- 和 5- 脱氮杂核黄素外，还获得了 7,8- 二甲基衍生物和 8-异丙基核黄素。在所有情况下，这些化合物的合成都是从适当取代的苯胺开始，该苯胺与核糖基链缩合，然后完成退火的三环结构。双去甲基和异丙基化合物的吸收最大值与核黄素相似（分别为 436 和 448 nm），而 1-去氮杂核黄素显示出红移吸收（λmax = 537 nm），而 5-去氮杂核黄素则显示出红移吸收（λmax = 400 纳米）。四种修饰的黄素化合物的中点电位 (E0') 通过电位滴定法测定，使用核黄素作为参考化合物。两种烷基改性黄素的负中点电位略低，而与参考化合物相比，两种脱氮化合物具有更多的负中点值。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  DOI：

  10.1002/ejoc.200800504
• 作为产物：
  描述：

  D-核糖 在 丙二腈 吡啶 、 sodium cyanoborohydride 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 97.75h， 生成 2',3',4',5'-tetra-O-acetyl-5-deazariboflavin
  参考文献：
  名称：

  Improved Chemical Syntheses of 1- and 5-Deazariboflavin

  摘要：

  The cofactor flavin adenine dinucleotide (FAD) is required for the catalytic activity of a large class of enzymes known as flavoenzymes. Because flavin cofactors participate in catalysis via a number of different mechanisms, isoalloxazine analogues are valuable for mechanistic studies. We report improved chemical syntheses for the preparation of the two key analogues, 5-deazariboflavin and 1-deazariboflavin.

  DOI：

  10.1021/jo049859f

文献信息

• Conversion of a Dehalogenase into a Nitroreductase by Swapping its Flavin Cofactor with a 5-Deazaflavin Analogue
  作者：Qi Su、Petrina A. Boucher、Steven E. Rokita

  DOI：10.1002/anie.201703628

  日期：2017.8.28

  formation of the hydroxylamine intermediates. Efficient use of these enzymes also requires a regenerating system for NAD(P)H to avoid the costs associated with this natural reductant. Iodotyrosine deiodinase is a member of the same structural superfamily as many nitroreductases but does not directly consume reducing equivalents from NAD(P)H, nor demonstrate nitroreductase activity. However, exchange

  天然和工程化的硝基还原酶很少支持将硝基芳族化合物完全还原成其胺产物，并且更典型地，转化仅限于羟胺中间体的形成。有效使用这些酶还需要NAD（P）H的再生系统，以避免与这种天然还原剂相关的成本。碘酪氨酸脱碘酶与许多硝基还原酶是同一结构超家族的成员，但不直接消耗NAD（P）H的还原当量，也不显示硝基还原酶活性。但是，将其黄素辅因子与5-deazaflavin类似物进行交换会极大地抑制其天然脱碘酶活性，并导致显着的硝基还原酶活性，从而在方便和廉价的NaBH 4存在下支持将其完全还原为胺产物。。
• Smit, P.; Stork, G. A.; van der Plas, H. C., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 538 - 543
  作者：Smit, P.、Stork, G. A.、van der Plas, H. C.、den Hartog, J. A. J.、van der Marel, G. A.、van Boom, J. H.

  DOI：——

  日期：——
• RNA aptamers that bind flavin and nicotinamide redox cofactors
  作者：Charles T. Lauhon、Jack W. Szostak

  DOI：10.1021/ja00109a008

  日期：1995.2

  RNA molecules that specifically bind riboflavin (Rb) and beta-nicotinamide mononucleotide (NMN) have been isolated by in vitro selection, A simple structural motif containing intramolecular G-quartets was found to bind tightly to oxidized riboflavin (K-d = 1-5 mu M) DNA versions of the consensus sequence also bind, but with weaker affinity. DMS protection experiments show that the quartet structure of these aptamers is stabilized by interaction with the flavin. As a measure of their redox specificity, the aptamers do not show significant differential binding between oxidized and reduced forms of a 5-deazariboflavin derivative that is a close structural analog of riboflavin. In contrast to the lack of redox specificity of the riboflavin aptamers, RNAs selected for binding to the nicotinamide portion of NAD discriminate between NAD and NADH in solution by over an order of magnitude. A mutagenized pool based on one of the NMN aptamer sequences was used to reselect for NMN binding. Comparison of the reselected sequences led to the identification of the binding region of the aptamer. A complex secondary structure containing two interacting stem-loops is proposed for the minimal NMN-binding RNA. The same mutagenized pool was used to select for increased discrimination between NMN and NMNH. From these reselected sequences, a mutation within the binding region was identified that increases specificity for NMN. These experiments show that RNA can bind these cofactors with low micromolar affinity and, in the case of nicotinamide cofactors, can discriminate between the two redox states. These cofactor binding motifs may provide a framework for generating new ribozymes that catalyze redox reactions similar to those found in basic metabolic pathways.