12-(4-硝基苯氧基)十二烷酸 | 230613-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 12-(4-硝基苯氧基)十二烷酸
• 英文名称: 12-(para-nitrophenoxy)dodecanoic acid
• 英文别名: 12-(4-Nitrophenoxy)dodecanoic acid
• CAS: 230613-81-7
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: SVQZCSVOBTWEFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-(4-硝基苯氧基)十二烷酸 在 cytochrome P₄₅₀ BM₃H F₈₇A 、 双氧水 作用下， 以 二甲基亚砜 为溶剂， 生成 对硝基苯酚 、 12-oxododecanoic acid
  参考文献：
  名称：

  Immobilization of P450 BM-3 monooxygenase on mesoporous molecular sieves with different pore diameters

  摘要：

  The immobilization of the isolated heme domain of P450 BM-3 (BM3H_F87A) on two mesoporous molecular sieves, MCM-41 (pore diameter 25 angstrom) and SBA-15 (pore diameter 60 angstrom and 133 angstrom) was examined systematically, and the activity of the immobilized enzyme toward para-nitrophenoxydodecanoic acid (12-pNCA) and n-octane was determined. Hydrogen peroxide was utilized as source of electrons and oxygen to support the monooxygenase activity of BM3H_F87A. The mesoporous materials were characterized by X-ray diffraction and nitrogen adsorption analyses before and after immobilization. The results revealed that the immobilization efficiency of MCM-41 and SBA-15 after single immersion was strongly affected by the pH value of the enzyme solution, initial enzyme concentration and agitation conditions. By modelling the 3D structure in silico and performing electrostatic potential calculations, the pH-dependence of the enzyme immobilization could be explained and a possible orientation of the protein on mesoporous materials was predicted. The oxidizing activity of the immobilized enzyme was found to depend on pore diameter and accessibility of the substrate for the enzyme. The highest activity toward 12-pNCA of 830 nmol product/mg P450/min was observed with BM3H_F87A immobilized on SBA-15 with pore diameter 133 angstrom. Enzyme activity toward n-octane was similar for the enzyme immobilized on SBA-15 of 60 angstrom and 133 angstrom. and was at least two-fold higher as compared to a system with free enzyme. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.01.020
• 作为产物：
  描述：

  12-溴十二烷酸 在 盐酸 、 水 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 12-(4-硝基苯氧基)十二烷酸
  参考文献：
  名称：

  DNA-Mediated Assembly of Cytochrome P450 BM3 Subdomains

  摘要：

  Cytochrome P450 BM3 is a versatile enzyme, which holds great promise for applications in biocatalysis and biomedicine. We here report on the generation of a hybrid DNA-protein device based on the two subdomains of BM3, the reductase domain BMR and the porphyrin domain BMP. Both subdomains were fused genetically to the HaloTag protein, a self-labeling enzyme, allowing for the bioconjugation with chloroalkane-modified oligonucleotides. The subdomain-DNA-chimeras could be reassembled by complementary oligonucleotides, thus leading to reconstitution of the monooxygenase activity of BM3 holoenzyme, as demonstrated by conversion of the reporter substrate 12-pNCA. Arrangement of the two chimeras on a switchable DNA scaffold allowed one to control the distance between both subdomains, as indicated by the DNA-dependent activity of the holoenzyme. Furthermore, a switchable chimeric device was constructed, in which monooxygenase activity could be turned off by DNA strand displacement. This study demonstrates that P450 BM3 engineering and strategies of DNA nanotechnology can be merged to open up novel ways for the development of novel screening systems or responsive catalysts with potential applications in drug delivery.

  DOI：

  10.1021/ja204993s

文献信息

• Cytochrome P450 oxygenases
  申请人：California Institute of Technology

  公开号：US20030100744A1

  公开（公告）日：2003-05-29

  Nucleic acids encoding cytochrome P450 variants are provided. The cytochrome P450 variants of have a higher alkane-oxidation capability, alkene-oxidation capability, and/or a higher organic-solvent resistance than the corresponding wild-type or parent cytochrome P450 enzyme. A preferred wild-type cytochrome P450 is cytochrome P450 BM-3. Preferred cytochrome P450 variants include those having an improved capability to hydroxylate alkanes and epoxidate alkenes comprising less than 8 carbons, and have amino acid substitutions corresponding to V78A, H236Q, and E252G of cytochrome P450 BM-3. Preferred cytochrome P450 variants also include those having an improved hydroxylation activity in solutions comprising co-solvents such as DMSO and THF, and have amino acid substitutions corresponding to T235A, R471A, E494K, and S1024E of cytochrome P450 BM-3.

  提供了编码细胞色素P450变体的核酸。这些细胞色素P450变体具有比相应的野生型或母体细胞色素P450酶更高的烷基氧化能力、烯烃氧化能力和/或更高的有机溶剂抗性。首选的野生型细胞色素P450是细胞色素P450 BM-3。首选的细胞色素P450变体包括那些具有改进的烷基羟化和烯烃环氧化能力，包括少于8个碳的，并且具有与细胞色素P450 BM-3的V78A、H236Q和E252G对应的氨基酸替换。首选的细胞色素P450变体还包括那些在包含DMSO和THF等共溶剂的溶液中具有改进的羟化活性，并具有与细胞色素P450 BM-3的T235A、R471A、E494K和S1024E对应的氨基酸替换。
• CYTOCHROME P450 OXYGENASES
  申请人：Farinas Edgardo T.

  公开号：US20120184015A1

  公开（公告）日：2012-07-19

  Nucleic acids encoding cytochrome P450 variants are provided. The cytochrome P450 variants of have a higher alkane-oxidation capability, alkene-oxidation capability, and/or a higher organic-solvent resistance than the corresponding wild-type or parent cytochrome P450 enzyme. A preferred wild-type cytochrome P450 is cytochrome P450 BM-3. Preferred cytochrome P450 variants include those having an improved capability to hydroxylate alkanes and epoxidate alkenes comprising less than 8 carbons, and have amino acid substitutions corresponding to V78A, H236Q, and E252G of cytochrome P450 BM-3. Preferred cytochrome P450 variants also include those having an improved hydroxylation activity in solutions comprising co-solvents such as DMSO and THF, and have amino acid substitutions corresponding to T235A, R471A, E494K, and S1024E of cytochrome P450 BM-3.

  提供了编码细胞色素P450变体的核酸。这些细胞色素P450变体具有比相应的野生型或亲本细胞色素P450酶更高的烷烃氧化能力、烯烃氧化能力和/或更高的有机溶剂耐受性。首选的野生型细胞色素P450是细胞色素P450 BM-3。首选的细胞色素P450变体包括那些具有改进的烷烃羟化和含有少于8个碳的烯烃环氧化能力，并且具有与细胞色素P450 BM-3的V78A、H236Q和E252G相对应的氨基酸替换。首选的细胞色素P450变体还包括那些在含有二甲亚砜和四氢呋喃等共溶剂的溶液中具有改进的羟化活性，并且具有与细胞色素P450 BM-3的T235A、R471A、E494K和S1024E相对应的氨基酸替换。
• Cytochrome P450 monooxygenase variants
  申请人：B.R.A.I.N. Biotechnology Research And Information Network AG

  公开号：EP2426198A1

  公开（公告）日：2012-03-07

  The present invention relates to a nucleic acid molecule encoding a polypeptide having cytochrome P450 monooxygenase activity, wherein said polypeptide comprises a reductase domain that deviates by at least one mutation from (a) the reductase domain of cytochrome P450 BM3, wherein the reductase domain of cytochrome P450 BM3 is represented by SEQ ID NO:1; or (b) a reductase domain having at least 95% sequence identity to SEQ ID NO: 1; and wherein said mutation(s) result(s) in an increased cytochrome P450 monooxygenase activity as compared to a polypeptide comprising the reductase domain of SEQ ID NO: 1. The present invention also relates to a vector comprising the nucleic acid molecule of the invention and a host transformed with the vector. Furthermore, the invention relates to a method of producing a polypeptide comprising culturing the host of the invention as well as to a polypeptide encoded by the nucleic acid molecule of the invention or produced by the method of the invention. The present invention further relates to the use of the polypeptide of the invention in biotransformation or fine chemical synthesis, to an oligo- or polynucleotide which specifically hybridizes to the nucleic acid molecule of the invention as well as to a composition and to a kit.

  本发明涉及一种编码具有细胞色素 P450 单加氧酶活性的多肽的核酸分子，其中所述多肽包括一个还原酶结构域，该还原酶结构域通过至少一个突变偏离(a) 细胞色素 P450 BM3 的还原酶结构域，其中细胞色素 P450 BM3 的还原酶结构域由 SEQ ID NO：1表示；或(b)与SEQ ID NO: 1具有至少95%序列同一性的还原酶结构域；并且与包含SEQ ID NO: 1还原酶结构域的多肽相比，所述突变导致细胞色素P450单加氧酶活性增加。本发明还涉及一种包含本发明核酸分子的载体和用该载体转化的宿主。此外，本发明还涉及一种生产多肽的方法，包括培养本发明的宿主以及由本发明的核酸分子编码或由本发明的方法生产的多肽。本发明还涉及本发明多肽在生物转化或精细化学合成中的用途，涉及与本发明核酸分子特异性杂交的寡核苷酸或多核苷酸，还涉及一种组合物和一种试剂盒。
• Labraries of optimized cytochrome P450 enzymes and the optimized P450 enzymes
  申请人：Arnold H. Frances

  公开号：US20050059045A1

  公开（公告）日：2005-03-17

  The present disclosure teaches that the recombination of homologous sequences of P450 enzymes, with the aid of SCHEMA to predict a resulting protein structure, is able to generate libraries of chimeras with significant functional diversity. Additionally, the members of these libraries demonstrate superior or unexpected new properties, which correlate with other factors that are observable in the library. Thus, the making of libraries of optimized P450 enzymes, the analysis of libraries to identify an optimized subset, and the optimized chimeras with improved or altered functionalities are all taught in the present disclosure.

  本公开的内容表明，借助 SCHEMA 预测所产生的蛋白质结构，P450 酶同源序列的重组能够产生具有显著功能多样性的嵌合体文库。此外，这些文库中的成员会表现出优越或意想不到的新特性，这些特性与文库中可观察到的其他因素相关。因此，制作优化 P450 酶文库、分析文库以确定优化子集以及具有改进或改变的功能的优化嵌合体都是本公开内容所教导的。
• NOVEL MONOOXYGENASE VARIANTS
  申请人：B.R.A.I.N. Biotechnology Research and Information Network AG

  公开号：EP2611912B1

  公开（公告）日：2016-11-02