17-epi-dammara-20(21),24-diene

• 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: 17-epi-dammara-20(21),24-diene
• 英文别名: (5S,8R,9R,10S,13R,14R,17R)-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• 化学式: C₃₀H₅₀
• 分子量: 410.727
• InChiKey: SEXOMBPXHYAKHY-MKMSBAOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  角鲨烯 在 squalene-hopene cyclase Phe₆₀₅Lys mutant 作用下， 生成 17-epi-dammara-20(21),24-diene
  参考文献：
  名称：

  Specific production of γ-polypodatetraene or 17-isodammara-20(21),24-diene by squalene–hopene cyclase mutant

  摘要：

  Amino acids lining the catalytic cavity of squalene-hopene cyclase of Alicyclobacillus acidocaldarius were mutated to investigate their catalytic functions. Mutagenesis of Leu607 to Lys in the central part of the cavity resulted in the production of the bicyclic gamma -polypodatetraene (1) as main product, while the mutation of Phe605 to Lys near the deprotonation site of the cavity led mainly to the formation of tetracyclic 17-isodammara-20(21),24-diene (2). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02149-3

文献信息

• New Cyclization Mechanism for Squalene: a Ring-expansion Step for the Five-membered C-ring Intermediate in Hopene Biosynthesis
  作者：Tsutomu HOSHINO、Masanori KOUDA、Takamasa ABE、Shumi OHASHI

  DOI：10.1271/bbb.63.2038

  日期：1999.1

  Three triterpenes having the 6/6/5-fused tri- and 6/6/6/5-fused tetracyclic skeletons were isolated from an incubation mixture of the mutated F601A enzyme, these products being in accordance with a Markovnikov closure. Successful trapping of the tricyclic cationic intermediate by using the squalene analog having a highly nucleophilic hydroxyl group leads us to propose that the ring expansion process

  从突变的F601A酶的温育混合物中分离出具有6/6 / 5-融合的三环和6/6/6 / 5-融合的四环骨架的三个三萜，这些产物与Markovnikov封闭法一致。通过使用具有高度亲核羟基的角鲨烯类似物成功捕获三环阳离子中间体，使我们提出5元C环的扩环过程涉及角鲨烯环化级联反应。
• On the cyclization mechanism of squalene: a ring expansion process of the five-membered D-ring intermediate
  作者：Tsutomu Sato、Tsutomu Hoshino、Takamasa Abe、Tsutomu Hoshino

  DOI：10.1039/a806948d

  日期：——

  Site-directed mutagenesis experiments with W169F, W169H and W489F for the squalene-hopene cyclase, and the formation of 10 possessing the five-membered D-ring and a tetrahydrofuran moiety as the enzyme product of the analogue 8 with a hydroxy group, strongly suggest that a ring expansion reaction from the five- to the six-membered ring is responsible for the D-ring formation of hopene.

  用 W169F、W169H 和 W489F 对角鲨烯-罂粟碱环化酶进行定点诱变实验，并在带有羟基的类似物 8 的酶产物中形成了具有五元 D 环和四氢呋喃分子的 10，这有力地表明，从五元环到六元环的扩环反应是形成罂粟碱 D 环的原因。
• <i>Alicyclobacillus acidocaldarius</i> Squalene‐Hopene Cyclase: The Critical Role of Steric Bulk at Ala306 and the First Enzymatic Synthesis of Epoxydammarane from 2,3‐Oxidosqualene
  作者：Natsumi Ideno、Shikou Umeyama、Takashi Watanabe、Mami Nakajima、Tsutomu Sato、Tsutomu Hoshino

  DOI：10.1002/cbic.201800281

  日期：2018.9.4

  SHC is widely conserved in known SHCs. Increases in steric bulk (A306T and A306V) led to the accumulation of 6,6,6,5‐fused tetracyclic scaffolds with 20R stereochemistry. This indicates folding of squalene in a chair‐chair‐chair‐boat conformation. The stereochemical fate in polycyclization is thus governed by the bulk at this position.

  Polycyclization和构象分析：Ala306在A.热硫化叶菌SHC广泛保守已知的特困家庭。空间体积（A306T和A306V）的增加导致具有20 R立体化学的6,6,6,5融合的四环支架的积累。这表明角鲨烯折叠成椅子-椅子-船构型。因此，多环化中的立体化学命运受该位置的主体支配。
• Functional analysis of Phe605, a conserved aromatic amino acid in squalene–hopene cyclases
  作者：Tsutomu Hoshino、Masanori Kouda、Takamasa Abe、Tsutomu Sato

  DOI：10.1039/b004129g

  日期：——

  Incubation of squalene with the site-directed mutant F605A of squalene–hopene cyclase from Alicyclobacillus acidocaldarius yielded many triterpenes consisting of the 6/6/5-fused tri-, 6/6/6/5-fused tetra-, and 6/6/6/6/5-fused pentacyclic skeletons, the function of F605 being assignable for facilitating the ring expansion and for stabilizing the hopanyl C22-cation, possibly via cation-π interactions.
• Specific production of γ-polypodatetraene or 17-isodammara-20(21),24-diene by squalene–hopene cyclase mutant
  作者：Susanne Schmitz、Christine Füll、Tobias Glaser、Klaus Albert、Karl Poralla

  DOI：10.1016/s0040-4039(00)02149-3

  日期：2001.1

  Amino acids lining the catalytic cavity of squalene-hopene cyclase of Alicyclobacillus acidocaldarius were mutated to investigate their catalytic functions. Mutagenesis of Leu607 to Lys in the central part of the cavity resulted in the production of the bicyclic gamma -polypodatetraene (1) as main product, while the mutation of Phe605 to Lys near the deprotonation site of the cavity led mainly to the formation of tetracyclic 17-isodammara-20(21),24-diene (2). (C) 2001 Elsevier Science Ltd. All rights reserved.