(+)-(1R,4R,5R)-5-exo-hydroxycamphor | 1126-88-1

• 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: (+)-(1R,4R,5R)-5-exo-hydroxycamphor
• 英文别名: 5-exo-hydrocy-1,7,7-trimethylbicyclo<3.2.1>heptan-2-one；5-exo-Hydroxycamphor；(1R)-5exo-hydroxy-bornan-2-one；(1R)-5exo-Hydroxy-bornan-2-on；(1R,4R,5R)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 1126-88-1；4367-83-3；13948-58-8；22285-79-6；107438-74-4；1607-84-7
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: DJQYBVLXBVJHMU-PJKMHFRUSA-N

物化性质

• 沸点：
  250.9±33.0 °C(predicted)
• 密度：
  1.107±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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

• 作为反应物：
  描述：

  (+)-(1R,4R,5R)-5-exo-hydroxycamphor 在 乙醚 、 silver carbonate 作用下， 生成 (1R)-5exo-(tetra-O-acetyl-β-D-glucopyranosyloxy)-bornan-2-one oxime
  参考文献：
  名称：

  Ishidate, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1929, vol. 49, p. 336,345; dtsch. Ref. S. 56, 60

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 (+)-(1R,4R,5R)-5-exo-hydroxycamphor
  参考文献：
  名称：

  Takeuchi, Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1933, vol. 23, p. 288,293

  摘要：

  DOI：

文献信息

• Engineering the haem monooxygenase cytochrome P450cam for monoterpene oxidation
  作者：Stephen G. Bell、Rebecca J. Sowden、Luet-Lok Wong

  DOI：10.1039/b100290m

  日期：——

  Monooxygenated terpenes are fine fragrance and flavouring chemicals, and active site mutants of the haem monooxygenase cytochrome P450cam which were designed to have improved complementarity between the substrate binding pocket and the monoterpenes (+)-α-pinene (1) and S-limonene (2) have been shown to have greatly enhanced activity for the oxidation of these two substrates, and the major products, verbenol and isopiperitenol from (1) and (2) respectively, were formed with high regioselectivity and near-total stereoselectivity.

  单氧化萜烯是精细香料和调味品化学物质，经过设计的血红素单氧化酶细胞色素P450cam的活性位点突变体在底物结合口袋和单萜(+)-α-蒎烯(1)及S-柠檬烯(2)之间实现了更好的互补性，已被证明对这两种底物的氧化具有显著增强的活性，并且主要产物分别为从(1)和(2)生成的芳樟醇和异薄荷脑，具有很高的区位选择性和接近完全的立体选择性。
• Engineering and improvement of the efficiency of a chimeric [P450cam-RhFRed reductase domain] enzyme
  作者：Aélig Robin、Gareth A. Roberts、Johannes Kisch、Federico Sabbadin、Gideon Grogan、Neil Bruce、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1039/b901716j

  日期：——

  A chimeric oxygenase, in which the P450cam domain was fused to the reductase host domains of a P450RhF from Rhodococcus sp. strain NCIMB 9784 was optimised to allow for a biotransformation at 30 mM substrate in 80% overall yield, with the linker region between P450 and FMN domain proving to be important for the effective biotransformation of (+)-camphor to 5-exo-hydroxycamphor.

  一种嵌合加氧酶，其中 P450cam 结构域与红球菌属 P450RhF 的还原酶宿主结构域融合。菌株 NCIMB 9784 经过优化，可在 30 mM 底物下进行生物转化，总产率为 80%，P450 和 FMN 结构域之间的接头区域被证明对于 (+)-樟脑有效生物转化为 5-外型-羟基樟脑非常重要。
• Cloning and Nucleotide Sequences of NADH-Putidaredoxin Reductase Gene (camA) and Putidaredoxin Gene (camB) Involved in Cytochrome P-450cam Hydroxylase of Pseudomonas putida1
  作者：Hideo Koga、Eiichi Yamaguchi、Kiyoshi Matsunaga、Hironori Aramaki、Tadao Horiuchi

  DOI：10.1093/oxfordjournals.jbchem.a122939

  日期：1989.11

  reductase and the entire camB gene encoding putidaredoxin. The 2.9 kbp CAM segment was adjacent to the 4.27 kbp HindIII CAM segment which has been previously cloned (Koga et al. (1986) J. Bacteriol. 166, 1089-1095). Thus, the total 7.17 kbp HindIII CAM directed all the genes responsible for early steps of D-camphor degradation, i.e. 5-exo-hydroxycamphor dehydrogenase (camD gene), cytochrome P-450cam (camC)

  携带编码参与D-樟脑降解途径的酶的CAM质粒的恶臭假单胞菌PpG1可以利用D-樟脑作为唯一碳源。细胞色素P-450cam和相关酶参与D-樟脑降解降解的早期氧化步骤。我们从PpG1的HindIII DNA文库中克隆了一个2.9 kbp的CAM片段，该片段携带着编码NADH-putidaredoxin还原酶的camA基因的主要部分和编码putidaredoxin的整个camB基因。2.9kbp的CAM区段与先前已克隆的4.27kbp的HindIII CAM区段相邻（Koga等人（1986）J.Bacteriol.166，1089-1095）。因此，总共7.17 kbp的HindIII CAM指导了负责D-樟脑降解的早期步骤的所有基因，即5-exo-hydroxy樟脑脱氢酶（camD基因），细胞色素P-450cam（camC），NADH-putidaredoxin还原酶（camA）和putida
• A Transmissible Plasmid Controlling Camphor Oxidation in <i>Pseudomonas putida</i>
  作者：J. G. Rheinwald、A. M. Chakrabarty、I. C. Gunsalus

  DOI：10.1073/pnas.70.3.885

  日期：1973.3

  Earlier papers demonstrated an extensive genetic exchange among fluorescent Pseudomonads; this one documents for genes specifying enzymes of peripheral dissimilation an extrachromosomal array, segregation, and frequent interstrain transfer. An hypothesis is presented of a general mechanism for the formation and maintenance of metabolic diversity. The example used, the path of oxidative cleavage of the carbocyclic rings of the bicyclic monoterpene D- and L-camphor, terminates in acetate release and isobutyrate chain debranching. By transduction, two gene linkage groups are shown for the reactions before and after isobutyrate. The group for reactions before isobutyrate is plasmid borne, contransferable by conjugation, mitomycin curable, and shows a higher segregation rate from cells that are multiplasmid rather than carrying a single plasmid. The genes that code for isobutyrate and essential anaplerotic and amphibolic metabolism are chromosomal. By conjugation plasmid-borne genes are transferred at a higher frequency than are chromosomal, and are transferred in homologous crosses more frequently than between heterologous species. Most isobutyrate-positive fluorescent pseudomonad strains will accept and express the camphor plasmid.

  早期的论文展示了荧光假单胞菌之间广泛的基因交换；本文记录了外染色体阵列、分离和频繁的菌株间转移的酶周边异化基因。提出了一种关于代谢多样性形成和维持的一般机制的假设。所使用的例子是二环单萜D-和L-蒎烷的碳环氧化裂解途径，终止于乙酸释放和异丁酸链去支。通过转导，显示了两个基因连锁群体，分别是异丁酸前和后的反应。异丁酸前的反应基因群体是质粒携带的，可通过接合共转移，丝菌素可治愈，并且从携带单一质粒的细胞中分离率较高。编码异丁酸和必需的补充代谢和两性代谢的基因是染色体上的。通过接合，质粒携带的基因的转移频率高于染色体，且在同源交叉中比异源物种之间更频繁地转移。大多数异丁酸阳性的荧光假单胞菌菌株将接受并表达蒎烷质粒。
• Complete nucleotide sequence of the 5-exo-hydroxycamphor dehydrogenase gene on the CAM plasmid of Pseudomonas putida (ATCC 17453)
  作者：Hironori Aramaki、Hideo Koga、Yasuhiro Sagara、Masaharu Hosoi、Tadao Horiuchi

  DOI：10.1016/0167-4781(93)90098-x

  日期：1993.7

  We determined the complete nucleotide sequence of the first gene of Pseudomonas putida cytochrome P-450cam hydroxylase operon, camD, which encodes 5-exo-hydroxycamphor dehydrogenase. This dehydrogenase apparently consists of 361 amino acids and has a molecular mass of 38.4 kDa. Structural relationships to other zinc-containing alcohol dehydrogenases also became evident.

  我们确定了恶臭假单胞菌细胞色素P-450cam羟化酶羟化酶操纵子camD的第一个基因的完整核苷酸序列，该基因编码5-exo-hydroxycamphor脱氢酶。该脱氢酶显然由361个氨基酸组成，分子量为38.4 kDa。与其他含锌醇脱氢酶的结构关系也变得明显。