香叶基焦磷酸铵盐 | 763-10-0

• 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
• 中文名称: 香叶基焦磷酸铵盐
• 中文别名: 牦牛儿基焦磷酸铵盐
• 英文名称: geranyl diphosphate
• 英文别名: GPP；geranyl pyrophosphate；Geranylpyrophosphat；geranyl-PP；[(2E)-3,7-dimethylocta-2,6-dienyl] phosphono hydrogen phosphate
• CAS: 763-10-0
• 化学式: C₁₀H₂₀O₇P₂
• 分子量: 314.212
• InChiKey: GVVPGTZRZFNKDS-JXMROGBWSA-N

物化性质

• 沸点：
  484.2±55.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)
• 闪点：
  20 °C
• 物理描述：
  Solid
• 碰撞截面：
  161.5 Ų [M-H2O-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 危险品标志：
  F,T
• 危险类别码：
  R23/24/25,R39/23/24/25,R11
• 危险品运输编号：
  UN 1230 3/PG 2
• 安全说明：
  S16,S23,S36/37,S45,S7
• 危险标志：
  GHS02,GHS06,GHS08
• 危险性描述：
  H225,H301 + H311 + H331,H370
• 危险性防范说明：
  P210,P260,P280,P301 + P310,P311

制备方法与用途

应用

香叶基焦磷酸盐主要包括香叶基焦磷酸铵盐，它是通过生物合成方法获得的法呢基焦磷酸盐。作为胆固醇、萜烯及萜类化合物合成过程中的一个关键中间体，香叶基焦磷酸铵盐在HMG-CoA还原酶途径中发挥着重要作用。

反应信息

• 作为反应物：
  描述：

  香叶基焦磷酸铵盐 在 magnesium chloride 、 manganese(ll) chloride 作用下， 以 甘油 为溶剂， 反应 14.0h， 生成 芳樟醇
  参考文献：
  名称：

  A domain swapping approach to elucidate differential regiospecific hydroxylation by geraniol and linalool synthases from perilla

  摘要：

  Geraniol and linalool are acyclic monoterpenes found in plant essential oils that have attracted much attention for their commercial use and in pharmaceutical studies. They are synthesized from geranyl diphosphate (GDP) by geraniol and linalool synthases, respectively. Both synthases are very similar at the amino acid level and share the same substrate; however, the position of the GDP to which they introduce hydroxyl groups is different. In this study, the mechanisms underlying the regiospecific hydroxylation of geraniol and linalool synthases were investigated using a domain swapping approach and sitedirected mutagenesis in perilla. Sequences of the synthases were divided into ten domains (domains I to IV-4), and each corresponding domain was exchanged between both enzymes. It was shown that different regions were important for the formation of geraniol and linalool, namely, domains IV-1 and -4 for geraniol, and domains III-b, III-d, and IV-4 for linalool. These results suggested that the conformation of carbocation intermediates and their electron localization were seemingly to be different between geraniol and linalool synthases. Further, five amino acids in domain IV-4 were apparently indispensable for the formation of geraniol and linalool. According to three-dimensional structural models of the synthases, these five residues seemed to be responsible for the different spatial arrangement of the amino acid at H524 in the case of geraniol synthase, while N526 is the corresponding residue in linalool synthase. These results suggested that the side-chains of these five amino acids, in combination with several relevant domains, localized the positive charge in the carbocation intermediate to determine the position of the introduced hydroxyl group. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.03.020
• 作为产物：
  描述：

  香叶醇 在 三溴化磷 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.75h， 生成 香叶基焦磷酸铵盐
  参考文献：
  名称：

  克拉维链霉菌（Streptomyces clavuligerus）1,8-桉树脑生物合成的详细视图。

  摘要：

  使用立体定向氘化的底物，研究了来自棒状链霉菌的细菌1,8-桉树脑合酶催化的环化反应的立体化学过程。与经过充分研究的丹参植物酶相反，该反应通过（S）-芳基二磷酸酯和（S）-萜品基阳离子进行，而最终环化反应在两种情况下都是同工加成，如孵育所示氧化氘中的（2-13C）香叶基二磷酸酯

  DOI：

  10.3762/bjoc.12.225
• 作为试剂：
  描述：

  (E)-2-(3-Indolyl)vinyl Isocyanide 在 香叶基焦磷酸铵盐 、 WelP₁ protein 、 magnesium chloride 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  ha吲哚型生物碱生物合成早期结构多样化的分子和遗传基础：welwitindolinone生产者中由WelU蛋白指导的12-上菲基吲哚U和12-上-八氟吲哚C的区域趋异组装

  摘要：

  从Wepal虹吸虫UTEX B1830和IC-52-3中的welwitindolinone途径中所有WelU蛋白的异源表达和纯化导致发现WelU1和WelU3选择性地组装12-表菲菲吲哚...

  DOI：

  10.1039/c7cc00782e

文献信息

• [EN] BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS<br/>[FR] COMPOSÉS BENZAMIDE OU BENZAMINE À UTILISER EN TANT QU'ANTICANCÉREUX POUR LE TRAITEMENT DE CANCERS HUMAINS
  申请人：UNIV TEXAS

  公开号：WO2017007634A1

  公开（公告）日：2017-01-12

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.

  所描述的发明提供了用于治疗对胆固醇生物合成抑制作出反应的肿瘤的小分子抗癌化合物。这些化合物选择性地抑制肿瘤来源的癌细胞中的胆固醇生物合成途径，但不影响正常分裂的细胞。
• Biochemical Investigations of Two 6-DMATS Enzymes from<i>Streptomyces</i>Reveal New Features of<scp>L</scp>-Tryptophan Prenyltransferases
  作者：Julia Winkelblech、Shu-Ming Li

  DOI：10.1002/cbic.201400046

  日期：2014.5.5

  6‐DMATSSa and 6‐DMATSSv from Streptomyces strains, in the presence of DMAPP and GPP. C6‐prenylated indole derivatives and dihydroxynaphthalenes with prenylation at the unsubstituted ring were identified as enzyme products of 6‐DMATSSa.

  他们可以做更多： 大号-色氨酸（1）和其衍生物以及羟基萘等2,3-二羟基萘（10）由6- DMATS被接受萨和6- DMATS SV从链霉菌属菌株，DMAPP的存在和GPP。C6-prenylated吲哚衍生物和未取代环上带有prenylation的二羟基萘被鉴定为6-DMATS Sa的酶产物。
• ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE
  申请人：Miyagi Yukino

  公开号：US20140171675A1

  公开（公告）日：2014-06-19

  The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):

  该发明涉及一种含有反式结构基团和顺式结构基团的异戊二烯寡聚物，可以用以下公式（1）表示，其中反式结构基团中至少有1个原子或基团被另一个原子或基团取代。该发明还涉及一种聚异戊二烯，它是使用异戊二烯寡聚物和异戊二烯二磷酸盐生物合成的。此外，该发明提供了一种橡胶组合物，包括异戊二烯寡聚物和/或聚异戊二烯，以及一种充气轮胎，其中轮胎组件（例如胎面和侧壁）由该橡胶组合物形成。 其中n表示1到10之间的整数；m表示1到30之间的整数；Y表示一个羟基、一个甲酰基、一个羧基、一个酯基、一个酰基或由以下公式（2）表示的基团。
• Modular Chemoenzymatic Synthesis of Terpenes and their Analogues
  作者：Luke A. Johnson、Alice Dunbabin、Jennifer C. R. Benton、Robert J. Mart、Rudolf K. Allemann

  DOI：10.1002/anie.202001744

  日期：2020.5.25

  amenable to large-scale production. Herein, we report a modular chemoenzymatic approach to synthesize terpene analogues from diphosphorylated precursors produced in quantitative yields. Through the addition of prenyl transferases, farnesyl diphosphates, (2E,6E)-FDP and (2Z,6Z)-FDP, were isolated in greater than 80 % yields. The synthesis of 14,15-dimethyl-FDP, 12-methyl-FDP, 12-hydroxy-FDP, homo-FDP

  非天然萜类化合物具有作为药物和农用化学品的潜力。然而，它们的化学合成通常是长的，复杂的，并且不易于大规模生产。在这里，我们报告了一种模块化的化学酶法，可以从以定量产量产生的二磷酸化前体中合成萜烯类似物。通过添加异戊二烯基转移酶，法呢基二磷酸（2E，6E）-FDP和（2Z，6Z）-FDP的分离率超过80％。还实现了14,15-二甲基-FDP，12-甲基-FDP，12-羟基-FDP，均-FDP和15-甲基-FDP的合成。这些改性的二磷酸酯与萜烯合酶一起使用，以生产非天然的倍半萜类化学信息素（S）-14,15-二甲基Germacrene D和（S）-12-甲基Germacrene D以及二氢青蒿素醛。
• [EN] MICROORGANISMS FOR PRODUCING 4C-5C COMPOUNDS WITH UNSATURATION AND METHODS RELATED THERETO<br/>[FR] MICRO-ORGANISMES POUR LA PRODUCTION DE COMPOSÉS EN 4C-5 C AVEC UNE INSATURATION ET PROCÉDÉS ASSOCIÉS
  申请人：GENOMATICA INC

  公开号：WO2016004334A1

  公开（公告）日：2016-01-07

  The invention provides a non-naturally occurring microbial organism having a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol, pathway. The microbial organism contains at least one exogenous nucleic acid encoding an enzyme in a pathway. The invention additionally provides a method for producing butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol,. The method can include culturing a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol-producing microbial organism, where the microbial organism expresses at least one exogenous nucleic acid encoding a pathway enzyme in a sufficient amount, and under conditions and for a sufficient period of time to produce butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol.

  该发明提供了一种具有丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇途径的非自然微生物生物体。该微生物生物体含有至少一个编码途径中酶的外源核酸。该发明还提供了一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的方法。该方法可以包括培养一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的微生物生物体，其中该微生物生物体表达至少一个编码途径酶的外源核酸，且在足够的量下，在适当的条件和足够的时间内产生丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇。