14,15-dihydrogeranylgeraniol

• 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: 14,15-dihydrogeranylgeraniol
• 英文别名: (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10-trien-1-ol
• 化学式: C₂₀H₃₆O
• 分子量: 292.505
• InChiKey: FDVXMRFDECGGBR-QIRCYJPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  14,15-dihydrogeranylgeraniol 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  探索GGTase-I底物要求。第2部分：新型饱和香叶基香叶基二磷酸类似物的合成及生化分析

  摘要：

  蛋白质异戊二烯化是一种翻译后修饰，可帮助某些蛋白质定位于血浆中的成员，并在这些成员中激活细胞信号传导。为了更好地了解类异戊二烯的需求和FTase和GGTase-I的差异，合成了一系列饱和的香叶基香叶基二磷酸二氢类似物，并针对哺乳动物FTase和GGTase-I进行了筛选。在我们的化合物库中，几种类似物被证明是GGTase-I的底物，与 GGPP（k rel  = 1.0）相比，11d的k rel = 0.95 。

  DOI：

  10.1016/j.bmcl.2016.06.035
• 作为产物：
  描述：

  E,E,E-12-hydroxyfarnesyl acetate 在 4-二甲氨基吡啶 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 14,15-dihydrogeranylgeraniol
  参考文献：
  名称：

  区域和立体异构的二氢和四氢香叶基香叶醇的制备以及天然（细菌）叶绿素中酯化基团的鉴定

  摘要：

  制备所有具有C 2 C 3双键的区域异构二-和四氢香叶基香叶醇作为真实样品。通过气相色谱法很好地分离了合成的C 20-异戊二烯醇。基于色谱分析，研究了香叶基香叶基的酶促还原途径，以鉴定光养生物中（细菌）叶绿素生物合成的最后阶段。通过从C10 C11到C10H C11（S）H的第一次区域和立体有择加氢，从C6 C7到C6H C7（S）H的第二次和第三C14 C15到C14H的区域和立体有针对性的加氢，将香叶基香叶基三倍还原为植酸基。C15H。还原序列的鉴定完成了天然存在的叶绿素a和细菌叶绿素a的生物合成途径，所述叶绿素a和细菌叶绿素a具有在17-丙酸酯残基中的酯化部分的植酸基。

  DOI：

  10.1016/j.bmc.2017.10.002

文献信息

• Functional Characterization and Cyclization Mechanism of a Diterpene Synthase Catalyzing the Skeleton Formation of Cephalotane‐Type Diterpenoids
  作者：Changkang Li、Shuai Wang、Xinxin Yin、Aobo Guo、Kebo Xie、Dawei Chen、Songyang Sui、Yaotian Han、Jimei Liu、Ridao Chen、Jungui Dai

  DOI：10.1002/anie.202306020

  日期：2023.8.14

  Cephalotene synthase (CsCTS), a new diterpene synthase from Cephalotaxus sinensis responsible for forming the core skeleton of cephalotane-type diterpenoids, was functionally identified. The cyclization cascade was studied in depth through isotopic labeling experiments and DFT calculations. Site-directed mutagenesis guided by molecular docking revealed the critical amino acid residues for the unique

  三尖杉烯合酶（CsCTS）是一种来自三尖杉的新二萜合酶，负责形成三尖杉烷型二萜类化合物的核心骨架，并得到了功能鉴定。通过同位素标记实验和DFT计算对环化级联进行了深入研究。由分子对接引导的定点诱变揭示了独特的碳正离子驱动级联环化机制的关键氨基酸残基。
• A novel geranylgeranyl reductase from the methanogenic archaeon<i>Methanosarcina acetivorans</i>displays unique regiospecificity
  作者：Takuya Ogawa、Keisuke Isobe、Takeshi Mori、Susumu Asakawa、Tohru Yoshimura、Hisashi Hemmi

  DOI：10.1111/febs.12851

  日期：2014.7

  Saturation of a prenyl group to various levels is a frequently observed modification of isoprenoids. The members of the geranylgeranyl reductase family, however, are the only known enzymes responsible for such reductive modifications in archaea. A methanogenic archaeon, Methanosarcina acetivorans, has proteins homologous to phytoene desaturase CrtI, which is the carotenogenic enzyme that catalyzes oxidation/isomerization of phytoene to lycopene, but their function in carotenogenesis is unlikely in a methanogen that does not produce carotenoids. In the present study, we identified one of the homologues, MA1492, as a new type of archaeal geranylgeranyl reductase that is not homologous to known geranylgeranyl reductases. The expression of MA1492 in Escherichia coli cells, which were genetically modified to produce unsaturated archaeal‐type lipids, led to the production of partially saturated lipid derivatives. Furthermore, we analyzed the substrate specificity of recombinant MA1492 via in vitro assays. The LC‐MS, or radio‐TLC, analysis of the reaction products showed that the enzyme was definitely specific to compounds containing C20 geranylgeranyl groups and reduced only one of four double bonds in a geranylgeranyl chain. The GC‐MS analysis of the product from geranylgeraniol confirmed that the reduction selectively occurred on the ω‐terminal double bond. The available crystallographic structure of an orthologue enzyme may explain the reaction mechanism that achieves the substrate specificity and regiospecificity.DatabaseMicrobial Genome Database (http://mbgd.genome.ad.jp/), EMBOSS Needle (https://www.ebi.ac.uk/Tools/psa/emboss_needle)
• Exploration of GGTase-I substrate requirements. Part 2: Synthesis and biochemical analysis of novel saturated geranylgeranyl diphosphate analogs
  作者：Kayla J. Temple、Elia N. Wright、Carol A. Fierke、Richard A. Gibbs

  DOI：10.1016/j.bmcl.2016.06.035

  日期：2016.8

  Protein prenylation is a type of post-translational modification that aids certain proteins in localizing to the plasma member where they activate cell signaling. To better understand the isoprenoid requirements and differences of FTase and GGTase-I, a series of saturated geranylgeranyl diphosphate analogs were synthesized and screened against both mammalian FTase and GGTase-I. Of our library of compounds

  蛋白质异戊二烯化是一种翻译后修饰，可帮助某些蛋白质定位于血浆中的成员，并在这些成员中激活细胞信号传导。为了更好地了解类异戊二烯的需求和FTase和GGTase-I的差异，合成了一系列饱和的香叶基香叶基二磷酸二氢类似物，并针对哺乳动物FTase和GGTase-I进行了筛选。在我们的化合物库中，几种类似物被证明是GGTase-I的底物，与 GGPP（k rel  = 1.0）相比，11d的k rel = 0.95 。
• Preparation of regio- and stereoisomeric di- and tetrahydrogeranylgeraniols and identification of esterifying groups in natural (bacterio)chlorophylls
  作者：Hitoshi Tamiaki、Kota Nomura、Tadashi Mizoguchi

  DOI：10.1016/j.bmc.2017.10.002

  日期：2017.12

  All regioisomeric di- and tetrahydrogeranylgeraniols possessing the C2C3 double bond were prepared as authentic samples. The synthetic C20-isoprenoid alcohols were separated well by gas chromatography. Based on the chromatographic analysis, the enzymatic reduction pathway of a geranylgeranyl group was investigated to identify the last stage of (bacterio)chlorophyll biosynthesis in phototrophs. The

  制备所有具有C 2 C 3双键的区域异构二-和四氢香叶基香叶醇作为真实样品。通过气相色谱法很好地分离了合成的C 20-异戊二烯醇。基于色谱分析，研究了香叶基香叶基的酶促还原途径，以鉴定光养生物中（细菌）叶绿素生物合成的最后阶段。通过从C10 C11到C10H C11（S）H的第一次区域和立体有择加氢，从C6 C7到C6H C7（S）H的第二次和第三C14 C15到C14H的区域和立体有针对性的加氢，将香叶基香叶基三倍还原为植酸基。C15H。还原序列的鉴定完成了天然存在的叶绿素a和细菌叶绿素a的生物合成途径，所述叶绿素a和细菌叶绿素a具有在17-丙酸酯残基中的酯化部分的植酸基。