5-exo-Hydroxy-(+/-)-Camphor | 154725-87-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-exo-Hydroxy-(+/-)-Camphor
• 英文别名: 5-exo-Hydroxy-(-)-Camphor；(-)-(1S, 4S,5S)-5-exo-hydroxycamphor；(1S,5S)-(-)-5-exo-hydroxycamphor；5-exo-hydroxycamphor；(1S)-5exo-hydroxy-bornan-2-one；(1S)-5exo-Hydroxy-bornan-2-on；(1S,4S,5S)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 154725-87-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: DJQYBVLXBVJHMU-MATHAZKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,4S,5S)-5-exo-hydroxycamphor 5-O-β-D-glucopyranoside 在 hesperidinase 作用下， 以 水 为溶剂， 反应 72.0h， 以1.3 mg的产率得到5-exo-Hydroxy-(+/-)-Camphor
  参考文献：
  名称：

  Terpene Glycosides and Cytotoxic Constituents from the Seeds ofAmomum xanthioides

  摘要：

  通过柱色谱分离 Amomum xanthioides 种子的 MeOH 提取物，得到了一种新的二萜糖苷 amoxanthoside A (1)，两种新的单萜糖苷 (1S,4S,5S)-5-exo-hydroxycamphor 5-O-β-D-glucopyranoside (2) 和 (1R,4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)、4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)，以及四种已知化合物：hedychiol A (4)、pygmol (5)、(1S,4R,6R)-(+)-6-endo-hydroxycamphor (6) 和 dihydroyashabushiketol (7)。新化合物的结构是通过光谱分析（包括大量二维核磁共振数据）确定的。利用磺胺 B 生物测定法测试了分离出的化合物对四种人类癌细胞系的体外细胞毒性。

  DOI：

  10.1055/s-0029-1186194

文献信息

• Structural Basis for Effector Control and Redox Partner Recognition in Cytochrome P450
  作者：Sarvind Tripathi、Huiying Li、Thomas L. Poulos

  DOI：10.1126/science.1235797

  日期：2013.6.7

  of oxidized and reduced P450cam complexed with its redox partner putidaredoxin (Pdx). Pdx favors binding to the more open form of P450cam, which enables establishment of the water-mediated H-bonded network required for proton-coupled electron transfer and O2 activation. The redox partner of P450cam stabilizes it in an open conformation to facilitate proton-coupled electron transfer. Cytochromes P450

  变得活跃 P450 细胞色素是一个酶家族，包含血红素辅因子并催化有机底物（包括药物）的氧化。需要蛋白质伙伴将电子传递给 P450。对这种机制的洞察来自对细菌 P450cam 的研究；然而，缺乏氧化还原配合物的结构阻碍了理解。特里帕蒂等人。(p. 1227) 描述了氧化和还原的 P450cam 与其氧化还原伙伴恶臭还蛋白 (Pdx) 复合的高分辨率晶体结构。Pdx 有利于与更开放的 P450cam 形式结合，从而能够建立质子耦合电子转移和 O2 激活所需的水介导的氢键网络。P450cam 的氧化还原伙伴将其稳定在开放构象中，以促进质子耦合电子转移。细胞色素 P450 催化各种单加氧酶反应，这些反应需要来自氧化还原伙伴的电子转移。尽管许多 P450 和少数氧化还原伙伴的结构是已知的，但关于氧化还原复合物的结构信息很少，因此我们对 P450-氧化还原伙伴相互作用的控制的理解存在差距。我们已经将氧化和还原的
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。
• BACTERIAL CYTOCHROME P450 PROTEIN VARIANT AND METHOD OF REDUCING CONCENTRATION OF FLUORINATED METHANE IN SAMPLE USING THE SAME
  申请人：Samsung Electronics Co., Ltd.

  公开号：EP3178922A1

  公开（公告）日：2017-06-14

  Provided is a recombinant microorganism including an exogenous gene encoding a bacterial cytochrome P450 protein or a variant thereof, a composition including the recombinant P450 protein or the variant thereof, which is used for removing CHnF4-n (n is an integer of 0 to 3) in a sample, and a method of reducing a concentration of CHnF4-n in the sample.

  本文提供了一种包括编码细菌细胞色素 P450 蛋白或其变体的外源基因的重组微生物、一种包括重组 P450 蛋白或其变体的组合物（用于去除样品中的 CHnF4-n（n 为 0 至 3 的整数））以及一种降低样品中 CHnF4-n 浓度的方法。
• In vivo and in vitro hydroxylation of cineole and camphor by cytochromes P450CYP101A1, CYP101B1 and N242A CYP176A1
  作者：Jeanette E. Stok、Emma A. Hall、Isobella S.J. Stone、Margaret C. Noble、Siew Hoon Wong、Stephen G. Bell、James J. De Voss

  DOI：10.1016/j.molcatb.2016.03.004

  日期：2016.6

  Cytochromes P450 (P450s) are valuable enzymes that can generate a range of useful compounds via biocatalytic oxidations that complement traditional synthetic chemistry. In this study three bacterial P450s, qP450(cam) (CYP101A1), CYP101B1 and the mutant N242A-P450(cin) (N242A-CYP176A1), were used to produce a range of products from the oxidation of the monoterpenes (1R)- and (1S) -camphor and 1,8-cineole. We demonstrate that both in vitro and in vivo catalytic turnover with these P450s can produce a complement of up to seven hydroxycamphors and seven hydroxycineoles, in addition to compounds produced from further oxidation. The CYP101B1 whole cell catalytic system was found to produce 300-600 mg/L of culture of oxidation products that could be easily separated chromatographically. The CYP101B1 in vitro oxidation of 1,8-cineole primarily produced (1S)-5 alpha-hydroxycineole, which was 78% of the total product formed. However, the amount of (1S)-5a-hydroxycineole was reduced to 42% of the total products when isolated from the CYP101B1 whole cell system. (1S)-6 alpha-Hydroxycineole (96% ee) could be isolated from a whole cell catalytic turnover of 1,8-cineole by N242A-P450c,n in a yield of 46 mg/L (98% of the total product). However, the amount of product isolated ((1R)-5-endo-hydroxycamphor, 75% of the total products) from the whole cell catalytic oxidation of (1R) -camphor with N242A-P450c,n was much lower (6 mg/L) due to the inefficient use of reducing equivalents (3.5 + 0.5%) for substrate oxidation. These compounds will assist in the identification of specific structures in mechanistic investigations and structure elucidation, but further optimisation is required to generate larger quantities for synthetic applications. (C) 2016 Elsevier B.V. All rights reserved.
• Molecular recognition in cytochrome P-450: alteration of regioselective alkane hydroxylation via protein engineering
  作者：William M. Atkins、Stephen G. Sligar

  DOI：10.1021/ja00189a057

  日期：1989.3