N-(6'-hydroxyhexyl)isoalloxazine | 316-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: N-(6'-hydroxyhexyl)isoalloxazine
• 英文别名: N-(10)-hydroxyhexyl flavin；10-(6-hydroxy-hexyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione；10-(ω-Hydroxy-hexyl)-7,8-dimethyl-isoalloxazin；10-(6-Hydroxyhexyl)-7,8-dimethylbenzo[g]pteridine-2,4-dione
• CAS: 316-10-9
• 化学式: C₁₈H₂₂N₄O₃
• 分子量: 342.398
• InChiKey: YLAMFRBBTBRECN-UHFFFAOYSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6'-hydroxyhexyl)isoalloxazine 在 亚磷酸 、 2,4,6-三异丙基苯磺酰氯 、 金刚烷酰氯 作用下， 以 吡啶 为溶剂， 反应 39.0h， 生成 [(2R,3S,5R)-2-[6-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)hexoxyphosphonoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  参考文献：
  名称：

  Method for Preparing New Flavin Derivatives:  Synthesis of Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts

  摘要：

  In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.

  DOI：

  10.1021/jo962361w
• 作为产物：
  描述：

  6-氯-1-己醇 在 DL-dithiothreitol 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 28.0h， 生成 N-(6'-hydroxyhexyl)isoalloxazine
  参考文献：
  名称：

  基于黄素的光驱动荧光探针，用于检测抗氧化氨基酸。

  摘要：

  我们合成了带有对甲苯磺酰基（Ts-OF）基团的黄素N（5）氧化物衍生物，作为“开启”荧光探针，用于检测多种抗氧化剂氨基酸和生物硫醇。以二硫苏糖醇为还原剂合成了氧化黄酮。在一些氨基酸和生物硫醇的存在下，例如组氨酸（His），蛋氨酸（Met），半胱氨酸（Cys），谷胱甘肽（GSH）和高半胱氨酸（Hcy），Ts-OF显示出光驱动的荧光增强。的1项1 H NMR研究表明所述的还原消去p甲苯磺酰基从TS-OF中抗氧化剂和光照射的存在。

  DOI：

  10.1002/open.201700144

文献信息

• Excess Electron Transfer in Flavin-Capped DNA-Hairpins
  作者：Christoph Behrens、Matthias Ober、Thomas Carell

  DOI：10.1002/1099-0690(200210)2002:19<3281::aid-ejoc3281>3.0.co;2-i

  日期：2002.10

  stacked in the intended fashion. Initial studies show that the flavin in the reduced and deprotonated state can indeed inject an electron into the hairpin. This flavin-capped DNA hairpin allows a detailed investigation of the excess electron transfer capabilities of double helical DNA. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  最近在头部带有电子受体分子的DNA发夹结构使Lewis和Wasielewski对双螺旋DNA的空穴电导率有了重要的了解。鉴于我们目前对破译双螺旋DNA多余的电子传输特性的兴趣，我们在本报告中评估了三种不同的黄素分子形成稳定的DNA发夹帽的能力。目的是构建新的DNA发夹，其中黄素发色团完美地堆叠在最终碱基对的顶部。固相合成协议是设计成用于三个flavin-掺入ħ -phosphonates成使用混合的亚磷酰胺/寡核苷酸ħ-膦酸酯/亚磷酰胺方案。我们在这里描述所有三个黄素帽分子产生稳定的DNA发夹。紫外线，荧光和熔融温度研究表明，三种黄素之一以预定的方式堆叠。初步研究表明，还原和去质子化状态的黄素确实可以将电子注入发夹中。这种黄素封端的DNA发夹可以对双螺旋DNA的过量电子转移能力进行详细研究。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）
• 放射性核素标记的苯并蝶啶类衍生物及其制 备方法和应用
  申请人：厦门大学

  公开号：CN108676007B

  公开（公告）日：2020-06-26

  本发明公开了放射性核素标记的苯并蝶啶类衍生物及其制备方法和应用，其分子结构式如下：本发明具有在发生脑卒中后立即给药并在给药后5min即进行显像诊断就能清晰地看到病灶部位，这极大缩短了诊断时间，在脑卒中的黄金抢救时间内进行正确诊断，能够及时指导有效治疗，达到治疗效果最好和风险最低，这对患者病情预后有着至关重要的作用。
• Model systems for flavoenzyme activity: a tuneable intramolecularly hydrogen bonded flavin–diamidopyridine complex
  作者：Alan S. F. Boyd、Joseph B. Carroll、Graeme Cooke、James F. Garety、Brian J. Jordan、Suhil Mabruk、Georgina Rosair、Vincent M. Rotello

  DOI：10.1039/b501887k

  日期：——

  We report the electrochemically tuneable intramolecular hydrogen bonding interactions between a covalently linked flavin-diamidopyridine unit.

  我们报告了共价连接的黄素-diamidopyridine单元之间的电化学可调分子内氢键相互作用。
• Model systems for flavoenzyme activity: flavin-functionalised SAMs as models for probing redox modulation through hydrogen bondingElectronic supplementary information (ESI) available: synthesis and spectroscopic details; cyclic voltammograms. See http://www.rsc.org/suppdata/cc/b3/b307980p/
  作者：Graeme Cooke、Florence M. A. Duclairoir、Phillip John、Neil Polwart、Vincent M. Rotello

  DOI：10.1039/b307980p

  日期：——

  We report the fabrication of flavin-functionalised self-assembled monolayers upon gold electrodes and their subsequent redox modulation via hydrogen bonding to 2,6-diethylamidopyridine.

  我们报告了在金电极上黄素官能化的自组装单层的制造及其随后通过氢键合到2,6-二乙基氨基吡啶的氧化还原调制。
• Method for Preparing New Flavin Derivatives:  Synthesis of Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts
  作者：Christelle Frier、Jean-Luc Décout、Marc Fontecave

  DOI：10.1021/jo962361w

  日期：1997.5.1

  In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.