cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate | 205652-50-2

• 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: cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate
• 英文别名: (5S,6R)-5,6-dihydroxy-4-propan-2-ylcyclohexa-1,3-diene-1-carboxylate
• CAS: 205652-50-2
• 化学式: C10H13O4-
• 分子量: 197.21
• InChiKey: BUZNWVREDOAOGD-DTWKUNHWSA-M

物化性质

• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会分解。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate 、 nicotinamide adenine dinucleotide 生成 2,3-Dihydroxy-p-cumate 、 氢(+1)阳离子 、 NADH
  参考文献：
  名称：

  p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon

  摘要：

  假单胞菌Pseudomonas putida F1利用对异丙基苯甲酸（p-cumate或p-异丙基苯甲酸）作为生长底物，通过一个八步的降解途径。一个长为35.75 kb的DNA片段，其中包含编码对p-cumate降解的cmt操纵子，被克隆成四个重叠的限制性片段，并用限制性内切酶进行了定位。通过检查携带这些片段和亚克隆片段的重组细菌中的酶活性，定位了编码p-cumate途径大多数酶的基因。随后对11,260 bp的序列分析给出了cmt操纵子的12个基因的精确位置。前三个基因cmtAaAbAc和第六个基因cmtAd编码p-cumate 2,3-双加氧酶（分别编码电子供体还原酶、终端双加氧酶的大亚基、终端双加氧酶的小亚基和电子供体）的组分；这些基因由编码2,3-二羟基-p-cumate 3,4-双加氧酶的cmtC分开，以及编码2,3-二羟基-2,3-二氢-p-cumate脱氢酶的cmtB。环裂解产物2-羟基-3-羧基-6-氧代-7-甲基辛-2,4-二烯酸被第七个基因cmtD编码的脱羧酶作用，后面是一个大的开放阅读框架cmtI，其功能不明。接下来的四个基因cmtEFHG编码2-羟基-6-氧代-7-甲基辛-2,4-二烯酸水解酶、2-羟基戊-2,4-二烯酸水合酶、4-羟基-2-氧代戊酸醛缩酶和乙醛脱氢酶，它们将脱羧产物转化为两性代谢中间产物。所有cmt基因产物的推断氨基酸序列，除了CmtD和CmtI外，在其他降解途径中催化类似反应的酶的氨基酸序列中具有可识别但较低水平的同源性。这种同源性最高的是途径的最后两个酶（4-羟基-2-氧代戊酸醛缩酶和乙醛脱氢酶[酰化]），它们与其他芳香族代谢途径相应的酶的同源性为66％至77％。发现携带cmt操纵子边界的某些限制性片段的重组细菌能够将吲哚转化为靛蓝。这个反应已知是由甲苯2,3-双加氧酶催化的，这导致发现编码甲苯降解的tod操纵子位于假单胞菌P. putida F1的cmt操纵子的下游2.8 kb处，并且方向相同。

  DOI：

  10.1128/jb.178.5.1351-1362.1996
• 作为产物：
  描述：

  氢(+1)阳离子 、 NADH 、 氧气 、 4-isopropylbenzoate anion 生成 cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate 、 nicotinamide adenine dinucleotide
  参考文献：
  名称：

  p-Cymene pathway in Pseudomonas putida: selective enrichment of defective mutants by using halogenated substrate analogs

  摘要：

  已经分离出了几类Pseudomonas putida（JT810）的突变体，这些突变体无法利用p-环甲基烷作为唯一的碳源。通过在含有p-环甲基烷（或p-香草酸）和各种卤代生长底物或代谢途径中间体的最小生长培养基中孵育细胞，选择性富集了突变体和被认为已经治愈降解性质粒的菌株。成功富集的类似物包括：p-氯甲苯，p-溴甲苯，α-氯-p-二甲苯和p-碘苯甲酸。突变株PpJT811，在与卤代类似物孵育后，比野生型亲本PpJT810显著地富集了缺陷突变体。建议采用一种p-环甲基烷代谢途径的遗传组织命名法。这些缺陷突变体被富集是因为它们所具有的遗传改变，这些改变使得克隆体在具有完整p-环甲基烷途径的情况下对类似物的转化执行了致命合成，从而获得了免疫力。

  DOI：

  10.1128/jb.143.2.816-824.1980

文献信息

• p-cymene pathway in Pseudomonas putida: initial reactions
  作者：J J DeFrank、D W Ribbons

  DOI：10.1128/jb.129.3.1356-1364.1977

  日期：1977.3

  Initial reactions of the p-cymene pathway induced in Pseudomonas putida PL have been reinvestigated. Oxidation of the methyl group attached to the nucleus occurs in three steps to give p-cumic acid. The substrate for the ring cleavage of 2,3-dihydroxy-p-cumate is formed from p-cumate in two reactions via a dihydrodiol intermediate (2,3-dihydroxy-4-isopropylcyclohexa-4,6-dienoate) and not as previously

  已对恶臭假单胞菌PL中诱导的p-cymene途径的初始反应进行了重新研究。连接到核上的甲基的氧化过程分为三个步骤，从而生成对-枯酸。2,3-二羟基-对-枯酸酯的环裂解的底物是在两个反应中通过二氢二醇中间体（2,3-二羟基-4-异丙基环己-4,6-二烯酸酯）由对-枯酸酯形成的，而不是以前那样通过3-羟基-对-甲酸酯推测。关于二氢二醇中间体的生理作用，有三方面的证据。（i）不能与p-cumate一起生长的恶臭假单胞菌PL-pT-11 / 43突变体，从p-cumate累积了一种化合物，该化合物被鉴定为2,3-二羟基-4-异丙基环己4 ，6-二羟乙酸。（II）该代谢物被烟酰胺腺嘌呤二核苷酸依赖性脱氢酶酶促氧化，该酶存在于野生型粗提物和回复株（PL-pT-11 / 43-R1）中，但在突变体中不存在。（iii）3-羟基-对-枯酸酯不支持P的生长。putida PL-W，并且不会被细胞或提取物氧化。
• p-Cymene pathway in Pseudomonas putida: selective enrichment of defective mutants by using halogenated substrate analogs
  作者：G J Wigmore、D W Ribbons

  DOI：10.1128/jb.143.2.816-824.1980

  日期：1980.8

  Several classes of mutants of Pseudomonas putida (JT810) defective in the utilization of p-cymene as sole carbon source have been isolated. Selective enrichment of the mutants and for strains putatively cured of a degradative plasmid was achieved by incubation of cells in minimal growth media containing p-cymene (or p-cumate) and various halogenated analogs of the growth substrates or pathway intermediates. Analogs which led to successful enrichments included: p-chlorotoluene, p-bromotoluene, alpha-chloro-p-xylene, and p-iodobenzoate. A mutant strain, PpJT811, constitutive for the p-cymene pathway gave significantly greater enrichments of defective mutants than the wild-type parent PpJT810 after incubation with the halogenated analogs. It is suggested that the defective mutants are enriched because of the genetic alterations they possess, which confer immunity to a lethal synthesis performed by transformation of the analogs in clones possessing an intact p-cymene pathway. A nomenclature for the genetic organization of p-cymene pathway is described.

  已经分离出了几类Pseudomonas putida（JT810）的突变体，这些突变体无法利用p-环甲基烷作为唯一的碳源。通过在含有p-环甲基烷（或p-香草酸）和各种卤代生长底物或代谢途径中间体的最小生长培养基中孵育细胞，选择性富集了突变体和被认为已经治愈降解性质粒的菌株。成功富集的类似物包括：p-氯甲苯，p-溴甲苯，α-氯-p-二甲苯和p-碘苯甲酸。突变株PpJT811，在与卤代类似物孵育后，比野生型亲本PpJT810显著地富集了缺陷突变体。建议采用一种p-环甲基烷代谢途径的遗传组织命名法。这些缺陷突变体被富集是因为它们所具有的遗传改变，这些改变使得克隆体在具有完整p-环甲基烷途径的情况下对类似物的转化执行了致命合成，从而获得了免疫力。
• Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids
  作者：R W Eaton、P J Chapman

  DOI：10.1128/jb.177.23.6983-6988.1995

  日期：1995.12

  The p-cumate-degrading strain Pseudomonas putida F1 and the m- and p-toluate-degrading strain P. putida mt-2 transform indole-2-carboxylate and indole-3-carboxylate to colored products identified here as indigo, indirubin, and isatin. A mechanism by which these products could be formed spontaneously following dioxygenase-catalyzed dihydroxylation of the indolecarboxylates is proposed. Indolecarboxylates

  降解p枯草杆菌的假单胞菌F1和降解腐殖酸对甲苯甲酸的p.mtida mt-2将吲哚2-羧酸盐和吲哚3-羧酸盐转化为有色产物，在此鉴定为靛蓝，靛玉红和Isatin。提出了一种机理，在吲哚羧酸酯的双加氧酶催化的二羟基化反应之后，这些产物可以自发​​形成。吲哚羧酸盐用作生色底物，用于鉴定携带编码p-枯草双加氧酶和甲苯二加氧酶的基因的重组细菌。带有双加氧酶基因的细菌可以很容易地在含有琼脂-2-羧酸盐或吲哚-3-羧酸盐的选择性琼脂平板上与其他无色重组大肠杆菌菌落区别为深绿色-蓝色菌落。
• p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon
  作者：R W Eaton

  DOI：10.1128/jb.178.5.1351-1362.1996

  日期：1996.3

  Pseudomonas putida F1 utilizes p-cumate (p-isopropylbenzoate) as a growth substrate by means of an eight-step catabolic pathway. A 35.75-kb DNA segment, within which the cmt operon encoding the catabolism of p-cumate is located, was cloned as four separate overlapping restriction fragments and mapped with restriction endonucleases. By examining enzyme activities in recombinant bacteria carrying these fragments and sub-cloned fragments, genes encoding most of the enzymes of the p-cumate pathway were located. Subsequent sequence analysis of 11,260 bp gave precise locations of the 12 genes of the cmt operon. The first three genes, cmtAaAbAc, and the sixth gene, cmtAd, encode the components of p-cumate 2,3-dioxygenase (ferredoxin reductase, large subunit of the terminal dioxygenase, small subunit of the terminal dioxygenase, and ferredoxin, respectively); these genes are separated by cmtC, which encodes 2,3-dihydroxy-p-cumate 3,4-dioxygenase, and cmtB, coding for 2,3-dihydroxy-2,3-dihydro-p-cumate dehydrogenase. The ring cleavage product, 2-hydroxy-3-carboxy-6-oxo-7-methylocta-2,4-dienoate, is acted on by a decarboxylase encoded by the seventh gene, cmtD, which is followed by a large open reading frame, cmtI, of unknown function. The next four genes, cmtEFHG, encode 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase, 2-hydroxypenta-2,4-dienoate hydratase, 4-hydroxy-2-oxovalerate aldolase, and acetaldehyde dehydrogenase, respectively, which transform the decarboxylation product to amphibolic intermediates. The deduced amino acid sequences of all the cmt gene products except CmtD and CmtI have a recognizable but low level of identity with amino acid sequences of enzymes catalyzing analogous reactions in other catabolic pathways. This identity is highest for the last two enzymes of the pathway (4-hydroxy-2-oxovalerate aldolase and acetaldehyde dehydrogenase [acylating]), which have identities of 66 to 77% with the corresponding enzymes from other aromatic meta-cleavage pathways. Recombinant bacteria carrying certain restriction fragments bordering the cmt operon were found to transform indole to indigo. This reaction, known to be catalyzed by toluene 2,3-dioxygenase, led to the discovery that the tod operon, encoding the catabolism of toluene, is located 2.8 kb downstream from and in the same orientation as the cmt operon in P. putida F1.

  假单胞菌Pseudomonas putida F1利用对异丙基苯甲酸（p-cumate或p-异丙基苯甲酸）作为生长底物，通过一个八步的降解途径。一个长为35.75 kb的DNA片段，其中包含编码对p-cumate降解的cmt操纵子，被克隆成四个重叠的限制性片段，并用限制性内切酶进行了定位。通过检查携带这些片段和亚克隆片段的重组细菌中的酶活性，定位了编码p-cumate途径大多数酶的基因。随后对11,260 bp的序列分析给出了cmt操纵子的12个基因的精确位置。前三个基因cmtAaAbAc和第六个基因cmtAd编码p-cumate 2,3-双加氧酶（分别编码电子供体还原酶、终端双加氧酶的大亚基、终端双加氧酶的小亚基和电子供体）的组分；这些基因由编码2,3-二羟基-p-cumate 3,4-双加氧酶的cmtC分开，以及编码2,3-二羟基-2,3-二氢-p-cumate脱氢酶的cmtB。环裂解产物2-羟基-3-羧基-6-氧代-7-甲基辛-2,4-二烯酸被第七个基因cmtD编码的脱羧酶作用，后面是一个大的开放阅读框架cmtI，其功能不明。接下来的四个基因cmtEFHG编码2-羟基-6-氧代-7-甲基辛-2,4-二烯酸水解酶、2-羟基戊-2,4-二烯酸水合酶、4-羟基-2-氧代戊酸醛缩酶和乙醛脱氢酶，它们将脱羧产物转化为两性代谢中间产物。所有cmt基因产物的推断氨基酸序列，除了CmtD和CmtI外，在其他降解途径中催化类似反应的酶的氨基酸序列中具有可识别但较低水平的同源性。这种同源性最高的是途径的最后两个酶（4-羟基-2-氧代戊酸醛缩酶和乙醛脱氢酶[酰化]），它们与其他芳香族代谢途径相应的酶的同源性为66％至77％。发现携带cmt操纵子边界的某些限制性片段的重组细菌能够将吲哚转化为靛蓝。这个反应已知是由甲苯2,3-双加氧酶催化的，这导致发现编码甲苯降解的tod操纵子位于假单胞菌P. putida F1的cmt操纵子的下游2.8 kb处，并且方向相同。