来自Streptomyces olindensis DAUFPE 562222 的不寻常的甲
Fernanda O Chagas1,2, Leandro M Garrido3, Raphael Conti1
1Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP 05508-070, Brazil.
Journal of natural products
|February 29, 2024
概括
菌株Streptomyces olindensis产生了新的重新排列的drimane sesquiterpenes,olindenones A-G. olindenone A的生物合成涉及甲基利酸盐路径和拟议的烯环酶介导的II型机制.
科学领域:
- 自然产品化学 自然产品化学
- 微生物的二次代谢物.
- 生物合成生物合成
背景情况:
- 在actinobacteria.glycosylated中,甘油酸是不常见的.
- 菌株Streptomyces olindensis DAUFPE 5622产生了一个新的类别的重新排列的drimane六烯:olindenones A-G.
- 奥林登 B-D 是氧化衍生物,而 E-G 是糖化的类似物.
研究的目的:
- 为了阐明olindenones的生物合成途径.
- 描述Streptomyces olindensis.产生的新型基.
- 为了研究四烯重新排列的机制.
主要方法:
- 13用于追踪代谢途径的C-同位素标记研究.
- 新型类的结构阐明.
- 生物信息分析以识别潜在的烯循环酶基因 (尽管在本研究中没有成功).
主要成果:
- 已证实,奥林登A生物合成通过甲基利二酸盐 (MEP) 途径发生.
- 有证据表明,奥林登A.的部分协调的重组机制.
- 提出了一种潜在的II型烯环酶介导机制,涉及碳酸驱动的循环和重新排列.
结论:
- 该研究提出了奥林登的详细生物合成路径,包括MEP路径和一种新的循环/重排机制.
- 负责奥林登生产的特定烯环酶基因仍未确定.
- 这项工作扩大了已知的类的多样性和它们在actinobacteria中的生物合成途径.
更多相关视频
相关概念视频
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Structure of Conjugated Dienes
5.1K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
5.1K
Diels–Alder Reaction: Characteristics of Dienes
4.1K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.1K
Diels–Alder Reaction: Characteristics of Dienophiles
6.1K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.1K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.2K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.2K


