3-heptanoyl-4-(hydroxymethyl)dihydrofuran-2(3H)-one | 119502-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-heptanoyl-4-(hydroxymethyl)dihydrofuran-2(3H)-one
• 英文别名: 3-Heptanoyl-4-(hydroxymethyl)oxolan-2-one
• CAS: 119502-27-1
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: NGQXDYJVORSCQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-heptanoyl-4-(hydroxymethyl)dihydrofuran-2(3H)-one 、 硼氢化钠 以4%的产率得到
  参考文献：
  名称：

  NIHIRA, TAKUYA;SHIMIZU, YOSHIHIRO;KIM, HYUN SOO;YAMADA, YASUHIRO, J. ANTIBIOTICS, 41,(1988) N2, C. 1828-1837

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-Dimethyl-5-(1-oxoheptyl)-1,3-dioxane-4,6-dione 在 甲酸 、 水 、 silica gel 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 18.5h， 生成 3-heptanoyl-4-(hydroxymethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  通过生物合成反应的复制，可以有效地合成灰链霉菌γ丁内酯自动诱导因子A因子†

  摘要：

  我们报告了链霉菌细菌的典型的γ-丁内酯信号化合物A因子的简明合成。类似于A因子生物合成中的酶促反应，我们的合成过程具有串联酯化作用-诺文agel缩合反应，生成2-酰基丁烯内酯，并使用以下方法使该α，β-不饱和羰基化合物产生令人惊讶的化学选择性共轭还原反应：氰基硼氢化钠。

  DOI：

  10.1039/c2ob06653j

文献信息

• Compositions and methods for activation and overexpression of secondary metabolites in microorganisms
  申请人：Prospective Research, Inc.

  公开号：US20180346871A1

  公开（公告）日：2018-12-06

  Methods and compositions herein provide non-naturally occurring γ-butyrolactones (GBLs) in racemic mixtures that increase efficiency and effectiveness of screening for production of antibiotics, and enhance yields and express silent pathways. Non-naturally occurring GBLs were synthesized and found to stimulate antibiotic production in several different streptomycete strains. Antibiotic production by Streptomyces coelicolor was induced by a racemic mixture of non-cognate stereoisomers of VB-D, seven of which are non-naturally occurring. Further, novel A-factor-type GBL analogs stimulated antibiotic production in S. coelicolor . Synthesis in response to the treatment with the non-cognates GBL was observed for known compounds including undecylprodigiosin, desferrioxamine and streptorubin B, as was synthesis of a compound of unknown structure. A group of 37 additional microbial strains was screened by principal component analysis to determine optimal concentrations of each of a panel of four non-cognate synthetic GBLs for addition to cultures with optimal stimulation of secondary metabolites, and large scale fermentations were analyzed and product enhancement by the GBLs was observed.

  本文提供的方法和组合物提供了非自然存在的γ-丁内酯（GBLs）的混合物，可增加筛选生产抗生素的效率和有效性，并增强产量和表达沉默途径。已合成非自然存在的GBLs，并发现它们能刺激几种不同链霉菌菌株的抗生素产生。通过非同源立体异构体VB-D的混合物（其中七种非自然存在）可以诱导链霉菌共色素的抗生素产生。此外，新型A因子型GBL类似物刺激了S. coelicolor的抗生素产生。已知化合物，包括十一烷基紫质素，去铁蛋白和链霉红素B，以及一种未知结构的化合物，对非同源GBL的处理作出了合成反应。通过主成分分析筛选了37个额外的微生物菌株，以确定每种四种非同源合成GBL的最佳浓度，以优化次生代谢物的刺激，并对大规模发酵进行了分析，观察到GBLs的产物增强效果。
• NIHIRA, TAKUYA;SHIMIZU, YOSHIHIRO;KIM, HYUN SOO;YAMADA, YASUHIRO, J. ANTIBIOTICS, 41,(1988) N2, C. 1828-1837
  作者：NIHIRA, TAKUYA、SHIMIZU, YOSHIHIRO、KIM, HYUN SOO、YAMADA, YASUHIRO

  DOI：——

  日期：——
• [EN] COMPOSITIONS AND METHODS FOR ACTIVATION AND OVEREXPRESSION OF SECONDARY METABOLITES IN MICROORGANISMS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR L'ACTIVATION ET LA SUREXPRESSION DE MÉTABOLITES SECONDAIRES DANS DES MICROORGANISMES
  申请人：PROSPECTIVE RES INC

  公开号：WO2017139429A1

  公开（公告）日：2017-08-17

  Methods and compositions herein provide non-naturally occurring γ-butyrolactones (GBLs) in racemic mixtures that increase efficiency and effectiveness of screening for production of antibiotics, and enhance yields and express silent pathways. Non-naturally occurring GBLs were synthesized and found to stimulate antibiotic production in several different streptomycete strains. Antibiotic production by Streptomyces coelicolor was induced by a racemic mixture of non-cognate stereoisomers of VB-D, seven of which are non-naturally occurring. Further, novel A-factor-type GBL analogs stimulated antibiotic production in S. coelicolor. Synthesis in response to the treatment with the non-cognates GBL was observed for known compounds including undecylprodigiosin, desferrioxamine and streptorubin B, as was synthesis of a compound of unknown structure. A group of 37 additional microbial strains was screened by principal component analysis to determine optimal concentrations of each of a panel of four non-cognate synthetic GBLs for addition to cultures with optimal stimulation of secondary metabolites, and large scale fermentations were analyzed and product enhancement by the GBLs was observed.
• Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus
  作者：Jesse B. Morin、Katherine L. Adams、Jason K. Sello

  DOI：10.1039/c2ob06653j

  日期：——

  A-factor, the prototypical γ-butyrolactone signalling compound of Streptomyces bacteria. In analogy to enzymatic reactions in A-factor biosynthesis, our synthesis features a tandem esterification–Knoevenagel condensation yielding a 2-acyl butenolide and a surprising, chemoselective conjugate reduction of this α,β-unsaturated carbonyl compound using sodium cyanoborohydride.

  我们报告了链霉菌细菌的典型的γ-丁内酯信号化合物A因子的简明合成。类似于A因子生物合成中的酶促反应，我们的合成过程具有串联酯化作用-诺文agel缩合反应，生成2-酰基丁烯内酯，并使用以下方法使该α，β-不饱和羰基化合物产生令人惊讶的化学选择性共轭还原反应：氰基硼氢化钠。