3,4-环硫丁腈 | 58130-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丙烷
• 中文名称: 3,4-环硫丁腈
• 英文名称: 1-cyano-2,3-epithiopropane
• 英文别名: Thiiraneacetonitrile；2-(thiiran-2-yl)acetonitrile
• CAS: 58130-93-1
• 化学式: C₄H₅NS
• 分子量: 99.1564
• InChiKey: BKIZJNMVTRYGSW-UHFFFAOYSA-N

物化性质

• 沸点：
  242.6±13.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)
• 保留指数：
  874

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  allylglucosinolate 在 thioglucosidase ferrous ammonium sulphate 、 DL-dithiothreitol 、 acetate buffer 、 epithiospecifier protein 、 sodium chloride 作用下， 反应 6.0h， 生成 3,4-环硫丁腈
  参考文献：
  名称：

  十字花科植物硫葡糖苷葡萄糖水解酶和表硫特异蛋白相互作用形成1-氰基表硫烷烃

  摘要：

  烯丙基硫代葡萄糖苷通过硫代葡萄糖苷葡萄糖水解酶和来自几个属的表硫特异性蛋白的相互作用转化为 1-氰基-2,3-表硫丙烷：芸苔属、克兰属、Armoracia 和 Sinapis。相互作用发生在遗传线之间，表明对表硫特异蛋白和硫葡糖苷葡萄糖水解酶的非特异性要求。

  DOI：

  10.1016/0031-9422(82)83011-2

文献信息

• Interactions of a fungal thioglucoside glucohydrolase and cruciferous plant epithiospecifier protein to form 1-cyanoepithioalkanes: implications of an allosteric mechanism
  作者：Richard J. Petroski、William F. Kwolek

  DOI：10.1016/s0031-9422(00)83521-9

  日期：1985.2

  Allylglucosinolate is converted to 1-cyano-2,3-epithiopropane by interaction of the thioglucoside glucohydrolase from the fungus Aspergillus sydowi QM 31c and the epithiospecifier protein from Crambe abyssinica . The kinetic evidence presented supports the hypothesis that the epithiospecifier protein interacts with thioglucoside glucohydrolase in an allosteric manner.

  摘要 通过来自真菌 Aspergillus sydowi QM 31c 的硫代葡萄糖苷葡萄糖水解酶和来自 Crambe abyssinica 的表硫特异性蛋白的相互作用，烯丙基硫代葡萄糖苷被转化为 1-氰基-2,3-环氧丙烷。所提供的动力学证据支持了这样的假设：epithiospecifier 蛋白以变构方式与硫葡糖苷葡萄糖水解酶相互作用。
• The intramolecular formation of epithioalkanenitriles from alkenylglucosinolates by Crambe abyssinica seed flour
  作者：Erich R. Brocker、M.H. Benn

  DOI：10.1016/s0031-9422(00)86982-4

  日期：1983.1

  Abstract Enzymatic degradations of mixtures of potassium 3-butenylgluco [1- 35 S]sinolate and allylglucosinolate by aqueous suspensions of Crambe abyssinica seed flour led to the formation of 4,5-epi[ 35 S]thiopentanenitrile and essentially unlabelled 3,4-epithiobutanenitrile. The formation of epithioalkanenitriles from alkenylglucosinolates is, therefore, deduced to be an intramolecular process.

  摘要 Crambe abyssinica 种子粉的水悬浮液对 3-丁烯基葡糖 [1- 35 S] 硫代葡萄糖酸钾和烯丙基硫代葡萄糖酸钾混合物的酶促降解导致形成 4,5-epi[ 35 S] 硫代戊腈和基本上未标记的 3,4-epithiobutanenitrile . 因此，从链烯基硫代葡萄糖苷形成环硫链烷腈被推定为分子内过程。
• The Arabidopsis Epithiospecifier Protein Promotes the Hydrolysis of Glucosinolates to Nitriles and Influences <i>Trichoplusia ni</i> Herbivory
  作者：Virginia Lambrix、Michael Reichelt、Thomas Mitchell-Olds、Daniel J. Kliebenstein、Jonathan Gershenzon

  DOI：10.1105/tpc.010261

  日期：2001.12

  Glucosinolates are anionic thioglucosides that have become one of the most frequently studied groups of defensive metabolites in plants. When tissue damage occurs, the thioglucoside linkage is hydrolyzed by enzymes known as myrosinases, resulting in the formation of a variety of products that are active against herbivores and pathogens. In an effort to learn more about the molecular genetic and biochemical regulation of glucosinolate hydrolysis product formation, we analyzed leaf samples of 122 Arabidopsis ecotypes. A distinct polymorphism was observed with all ecotypes producing primarily isothiocyanates or primarily nitriles. The ecotypes Columbia (Col) and Landsberg erecta (Ler) differed in their hydrolysis products; therefore, the Col × Ler recombinant inbred lines were used for mapping the genes controlling this polymorphism. The major quantitative trait locus (QTL) affecting nitrile versus isothiocyanate formation was found very close to a gene encoding a homolog of a Brassica napus epithiospecifier protein (ESP), which causes the formation of epithionitriles instead of isothiocyanates during glucosinolate hydrolysis in the seeds of certain Brassicaceae. The heterologously expressed Arabidopsis ESP was able to convert glucosinolates both to epithionitriles and to simple nitriles in the presence of myrosinase, and thus it was more versatile than previously described ESPs. The role of ESP in plant defense is uncertain, because the generalist herbivore Trichoplusia ni (the cabbage looper) was found to feed more readily on nitrile-producing than on isothiocyanate-producing Arabidopsis. However, isothiocyanates are frequently used as recognition cues by specialist herbivores, and so the formation of nitriles instead of isothiocyanates may allow Arabidopsis to be less apparent to specialists.

  硫代葡萄糖苷是阴离子硫代葡萄糖苷，已成为植物防御代谢物中最常被研究的类别之一。当组织受损时，硫代葡萄糖苷键会被一种名为芥子酶的酶水解，从而形成多种对食草动物和病原体具有活性的产物。为了进一步了解硫代葡萄糖苷水解产物形成的分子遗传和生化调控，我们对122种拟南芥生态型的叶片样本进行了分析。我们发现，所有生态型都表现出明显的多态性，它们主要产生异硫氰酸酯或腈。哥伦比亚（Col）和兰茨贝格直立（Ler）生态型的水解产物不同，因此，我们使用Col×Ler重组自交系来绘制控制这种多态性的基因。我们发现，影响腈和异硫氰酸酯形成的主要数量性状位点（QTL）非常接近编码油菜素内酯类同源蛋白（ESP）的基因，在某些十字花科植物的种子中，该蛋白在硫代葡萄糖苷水解过程中会导致形成表硫腈而不是异硫氰酸酯。异源表达的拟南芥ESP能够在芥子酶的作用下将硫代葡萄糖苷转化为表硫腈和简单腈，因此它比之前描述的ESP更具通用性。
• The Genetic Basis of Constitutive and Herbivore-Induced ESP-Independent Nitrile Formation in Arabidopsis    
  作者：Meike Burow、Anja Losansky、René Müller、Antje Plock、Daniel J. Kliebenstein、Ute Wittstock

  DOI：10.1104/pp.108.130732

  日期：2009.1.6

  activities, are formed at the expense of isothiocyanates. Recently, simple nitriles were recognized to serve distinct functions in plant-insect interactions. Here, we show that simple nitrile formation in Arabidopsis (Arabidopsis thaliana) ecotype Columbia-0 rosette leaves increases in response to herbivory and that this increase is independent of the known epithiospecifier protein (ESP). We combined

  芥子油苷是一组硫代葡萄糖苷，它们是十字花科植物中发现的一种活化的化学防御物。植物组织损伤导致芥子油苷被称为黑芥子酶的内源性硫葡糖苷酶水解。糖苷的自发重排产生对许多生物有毒的反应性异硫氰酸酯。在存在区分蛋白的情况下，以异硫氰酸酯为代价，形成了具有不同生物活性的替代产物，即表硫腈，简单腈和硫氰酸酯。最近，人们认识到简单的腈在植物与昆虫的相互作用中具有独特的功能。这里，我们显示，在拟南芥（Arabidopsis thaliana）生态型Columbia-0莲座叶中，简单的腈形成响应草食动物而增加，并且这种增加独立于已知的EpithioSPecifier蛋白（ESP）。我们结合了系统发育分析，拟南芥突变体的筛选，重组蛋白表征和表达定量性状基因座定位，以鉴定编码负责在哥伦比亚-0莲座叶中组成性和食草动物诱导的简单腈形成的腈-指定蛋白（NSP）的基因。 。AtNSP1是五个拟南芥ESP同源物之一，可促
• Glucosinolate hydrolysis in Lepidium sativum––identification of the thiocyanate-forming protein
  作者：Meike Burow、Andrea Bergner、Jonathan Gershenzon、Ute Wittstock

  DOI：10.1007/s11103-006-9071-5

  日期：2006.12.7

  Glucosinolates are a class of thioglycosides found predominantly in plants of the order Brassicales whose function in anti-herbivore defense has been attributed to the products formed by myrosinase-catalyzed hydrolysis upon plant tissue damage. The most common type of hydrolysis products, the isothiocyanates, are toxic to a wide range of organisms. Depending on the glucosinolate side-chain structure and the presence of certain protein factors, other types of hydrolysis products, such as simple nitriles, epithionitriles and organic thiocyanates, can be formed whose biological functions are not well understood. Of the proteins controlling glucosinolate hydrolysis, only epithiospecifier proteins (ESPs) that promote the formation of simple nitriles and epithionitriles have been identified on a molecular level. We investigated glucosinolate hydrolysis in Lepidium sativum and identified a thiocyanate-forming protein (TFP) that shares 63-68% amino acid sequence identity with known ESPs and up to 55% identity with myrosinase-binding proteins from Arabidopsis thaliana, but differs from ESPs in its biochemistry. TFP does not only catalyze thiocyanate and simple nitrile formation from benzylglucosinolate but also the formation of simple nitriles and epithionitriles from aliphatic glucosinolates. Analyses of glucosinolate hydrolysis products in L. sativum autolysates and TFP transcript accumulation revealed an organ-specific regulation of thiocyanate formation. The identification of TFP defines a new family of proteins that control glucosinolate hydrolysis and challenges the previously proposed reaction mechanism of epithionitrile formation. As a protein that promotes the formation of a wide variety of hydrolysis products, its identification provides an important tool for further elucidating the mechanisms of glucosinolate hydrolysis as well as the ecological role and the evolutionary origin of the glucosinolate-myrosinase system.

  硫代葡萄糖苷是一类主要存在于十字花科植物中的硫代糖苷，其抗食草动物的作用归因于植物组织受损时由芥子酶催化水解形成的产品。最常见的异硫氰酸盐水解产物对多种生物有毒。根据硫代葡萄糖苷侧链结构和某些蛋白质因子的存在，可以形成其他类型的水解产物，如简单腈、表硫腈和有机硫氰酸盐，其生物学功能尚不明确。在控制硫代葡萄糖苷水解的蛋白质中，只有促进形成简单腈和表硫腈的表硫苷酶蛋白（ESP）在分子水平上得到了确认。我们研究了甘蓝中的硫代葡萄糖苷水解，并鉴定了一种形成硫氰酸盐的蛋白（TFP），该蛋白与已知的ESP具有63-68%的氨基酸序列相似性，与拟南芥中的芥子酶结合蛋白具有高达55%的相似性，但在生物化学上与ESP不同。TFP不仅催化苄基硫代葡萄糖苷形成硫氰酸盐和简单腈，还催化脂肪族硫代葡萄糖苷形成简单腈和表硫腈。对甘蓝自溶产物中硫代葡萄糖苷水解产物