7-O-geranyl genistein | 1072940-14-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-O-geranyl genistein
• 英文别名: 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 1072940-14-7
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: BTRGJSAFPNJFGK-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香叶基焦磷酸铵盐 、 染料木素 在 Tris-HCl buffer 、 magnesium chloride 作用下， 生成 7-O-geranyl genistein
  参考文献：
  名称：

  Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities

  摘要：

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.052

文献信息

• Novel aromatic prenyltransferases, nucleic acids encoding same and uses therefor
  申请人：Kuzuyama Tomohisa

  公开号：US20060183211A1

  公开（公告）日：2006-08-17

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.

  根据本发明，一种新型芳香族前基转移酶 Orf2 来自于 链霉菌 菌株 CL190 中发现的一种参与萘素生物合成的新型芳香族前基转移酶 Orf2，并阐明了其结构。这种炔基转移酶催化炔基与含有芳香核的化合物之间形成 C-C 键，同时还具有形成 C-O 键的活性。前炔基转移酶的许多晶体结构已得到解决和完善，例如：（1）前炔基转移酶与缓冲分子（TAPS）的复合物；（2）前炔基转移酶与二磷酸香叶酯（GPP）和 Mg 2+ 和 (3) 1,6-二羟基萘（1,6-DHN）或 (4) 黄素（即 2,5,7-三羟基-1,4-萘醌，它是 1,3,6,8-四羟基萘（THN）的氧化产物）的三元复合物。这些结构已分别求解并精炼至 1.5 Å、2.25 Å、1.95 Å 和 2.02 Å。这是首个芳香族预烯基转移酶的结构，显示出一种意想不到的非经典（β/α）桶状结构。与芳香底物和含预烯醇底物及类似物的复合物划定了活性位点，并与所提出的预烯醇基团转移的亲电机制相一致。这些结构还为了解这一结构独特的芳香族前酰基转移酶家族的前酰基链长决定和芳香族共底物识别提供了机理基础。这些结构信息有助于预测蛋白质的芳香族前基转移酶活性。
• NOVEL AROMATIC PRENYLTRANSFERASES, NUCLEIC ACIDS ENCODING SAME AND USES THEREFOR
  申请人：Kuzuyama Tomohisa

  公开号：US20080274478A1

  公开（公告）日：2008-11-06

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.
• US7361483B2
  申请人：——

  公开号：US7361483B2

  公开（公告）日：2008-04-22
• US7544498B2
  申请人：——

  公开号：US7544498B2

  公开（公告）日：2009-06-09
• US8124390B2
  申请人：——

  公开号：US8124390B2

  公开（公告）日：2012-02-28