scytalone | 49598-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: scytalone
• 英文别名: 3,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenone；(3S)-3,6,8-trihydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 49598-85-8
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: RTWVXIIKUFSDJB-ZETCQYMHSA-N

物化性质

• 沸点：
  476.7±34.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  scytalone 在 氢氧化钾 、 氧气 作用下， 以 乙醇 为溶剂， 生成 2-羟基胡桃醌
  参考文献：
  名称：

  黄萎病菌的Pentaketide代谢产物：（+）-scytalone作为黑色素的天然前体的鉴定

  摘要：

  黄萎病菌的棕色brm -1突变体的培养滤液。当添加到10个白化突变体的平板培养物中时，恢复了正常的黑色素（黑色素）合成。通过物理特性（mp，UV，IR，NMR，MS）和化学性质分离出活性代谢物，并将其鉴定为（+）-辛酮[3,4-dihydro-3,6,8-trihydroxy-1（2H）萘]。转换。还分离并鉴定了相关的代谢物黄素蛋白和顺式羟基cytalone 。黄病毒素及其衍生物有助于brm -1突变体的红棕色。赛蜜可能是真菌中黑色素生物合成的一般中间体。

  DOI：

  10.1016/0040-4020(76)85009-0

文献信息

• FUNGI TRANSFORMANT FOR MELANIN PRODUCTION AND USES THEREOF
  申请人：Tzean Min-Nan

  公开号：US20110158970A1

  公开（公告）日：2011-06-30

  The present invention cloned melanin biosynthesis genes encoding polyketide synthase (PKS), scytalone dehydratase (SCD) and 1.3.8-trihydroxynaphthalene reductase (THN) from the dematiaceous Alternasia alternate into plasmid pCAMBIA1300, followed by transformation of the plasmid into Matarhizium anisopliae via Agrobacterium tumefaciens -mediated transformation. The transformant was able to express the abovementioned genes and synthesize melanin, which then showed enhanced UV tolerance. The transcription and expression of these melanin genes were confirmed in several pathways. The tolerances toward UV radiation, drought and high temperature were increased significantly in these transformants. In addition, the host insects were more susceptible to these transformants under UV radiation.

  本发明将黑色素合成基因聚酮合酶（PKS）、赤霉烷醇脱水酶（SCD）和1.3.8-三羟基萘醌还原酶（THN）从黑色素菌Alternaria alternate中克隆到质粒pCAMBIA1300中，然后通过农杆菌介导转化将质粒转化到拟革菌Matarhizium anisopliae中。转化体能够表达上述基因并合成黑色素，进而表现出增强的紫外线耐受性。这些黑色素基因的转录和表达在多个途径中得到了确认。这些转化体对紫外线辐射、干旱和高温的耐受性显著提高。此外，在紫外线辐射下，寄主昆虫更容易受到这些转化体的影响。
• Fungi transformant for melanin production and uses thereof
  申请人：Tseng Min-Nan

  公开号：US08518393B2

  公开（公告）日：2013-08-27

  The present invention cloned melanin biosynthesis genes encoding polyketide synthase (PKS), scytalone dehydratase (SCD) and 1.3.8-trihydroxynaphthalene reductase (THN) from the dematiaceous Alternasia alternate into plasmid pCAMBIA1300, followed by transformation of the plasmid into Matarhizium anisopliae via Agrobacterium tumefaciens-mediated transformation. The transformant was able to express the abovementioned genes and synthesize melanin, which then showed enhanced UV tolerance. The transcription and expression of these melanin genes were confirmed in several pathways. The tolerances toward UV radiation, drought and high temperature were increased significantly in these transformants. In addition, the host insects were more susceptible to these transformants under UV radiation.

  本发明从黑色素生物合成中克隆了聚酮合酶（PKS）、赤藓烯脱水酶（SCD）和1.3.8-三羟基萘还原酶（THN）编码基因，并将其导入质粒pCAMBIA1300中，随后通过农杆菌介导转化将质粒转化到拟南芥茵蝇霉中。转化体能够表达上述基因并合成黑色素，从而表现出增强的紫外线耐受性。这些黑色素基因的转录和表达在多个途径中得到了确认。这些转化体对紫外线辐射、干旱和高温的耐受性显著提高。此外，在紫外线辐射下，寄主昆虫更容易受到这些转化体的影响。
• Enzymatic Characterization of Scytalone Dehydratase Val75Met Variant Found in Melanin Biosynthesis Dehydratase Inhibitor (MBI-D) Resistant Strains of the Rice Blast Fungus
  作者：Naoki YAMADA、Takayuki MOTOYAMA、Masayoshi NAKASAKO、Shinzo KAGABU、Toshiaki KUDO、Isamu YAMAGUCHI

  DOI：10.1271/bbb.68.615

  日期：2004.1

  2-dichloro-N-[(R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide) is a potent chemical against the rice blast fungus, Pyricularia oryzae. In 2001, isolates of the fungus with reduced sensitivity to this fungicide appeared in Saga Prefecture of Japan and were regarded as a potential threat to rice protection by carpropamid. The cause of the resistance has been identified genetically as a point mutation

  杀虫ami（（1RS，3SR）-2,2-二氯-N-[（R）-1-（4-氯苯基）乙基] -1-乙基-3-甲基环丙烷甲酰胺）是一种有效的化学物质，可抵御稻瘟病真菌Pyricularia水稻 2001年，对这种杀真菌剂的敏感性降低的真菌分离株出现在日本佐贺县，被认为是对杀虫剂保护稻米的潜在威胁。从基因上已经确定了抗药性的原因是点突变，该突变导致断枝冬酰胺脱水酶中的Val75Met发生变化，这是杀菌剂的主要靶标。我们构建了变体酶的过表达系统，并表征了在催化过程中的动力学以及对甲酰胺异构体的抑制作用。变体酶保留了显着水平的酶活性。与野生型相比，丙酰胺对变异酶的抑制作用降低了200倍以上。基于这些结果，在这里我们提出了变异酶在保持正常酶活性方面的抗丙胺的可能机制。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Pentaketide metabolites of verticillium dahliae
  作者：A.A. Bell、R.D. Stipanovic、J.E. Puhalla

  DOI：10.1016/0040-4020(76)85009-0

  日期：1976.1

  of the brown brm-1 mutant of Verticillium dahliae Kleb. restored normal black pigment (melanin) synthesis when added to plate cultures of 10 albino mutants. The active metabolite was isolated and identified as (+)-scytalone [3,4-dihydro-3,6,8-trihydroxy-1(2H)naphthalenone] by physical characteristics (m.p., UV, IR, NMR, MS) and chemical conversions. Related metabolites, flaviolin and cis-hydroxyscytalone

  黄萎病菌的棕色brm -1突变体的培养滤液。当添加到10个白化突变体的平板培养物中时，恢复了正常的黑色素（黑色素）合成。通过物理特性（mp，UV，IR，NMR，MS）和化学性质分离出活性代谢物，并将其鉴定为（+）-辛酮[3,4-dihydro-3,6,8-trihydroxy-1（2H）萘]。转换。还分离并鉴定了相关的代谢物黄素蛋白和顺式羟基cytalone 。黄病毒素及其衍生物有助于brm -1突变体的红棕色。赛蜜可能是真菌中黑色素生物合成的一般中间体。