催化不对称的格里塞米辛的总合成,一个Thioangucycline多基基化物
Kincade Stevenson1, Dylan P Moran1, Thomas J Maimone1
1Department of Chemistry, University of California-Berkeley, 826 Latimer Hall, Berkeley, California 94720, United States.
研究人员合成了格里西米辛,一种罕见的含硫的安古西克林天然产品. 这项研究揭示了一种潜在的非酶途径,用于利用甲乙醇形成其独特的子结构.
科学领域:
- 自然产品化学 自然产品化学
- 有机合成 有机合成
- 生物化学 生物化学
背景情况:
- 安古西克林天然产品是一个主要的芳香多基基类.
- 硫酸环素,含硫的环素,是罕见的和未被充分研究的.
- 在2016年分离的格里塞米辛是一种独特的thioangucycline,其生物合成起源不明.
研究的目的:
- 为了实现第一个格里西米辛在以丰富形式的全合成.
- 为了研究格里塞米独特的结构和功能组的生物合成起源.
- 为了探索潜在的非酶性途径,以 thioangucycline 的形成.
主要方法:
- 使用先进的有机化学技术,全合成格里塞米.
- 选择性合成以获得特定的立体同位素.
- 机理学研究探讨甲基硫化物组和子骨的形成.
主要成果:
- 成功合成了以丰富形式的灰素.
- 证明了中的骨架可以从基因编码的安古西克林迈克尔接受器中形成.
- 表明甲乙醇和氧化剂可以在没有酶干预的情况下促进这种组合.
结论:
- 总合成提供了一条可靠的途径到格里塞米辛及其类似物.
- 这些发现表明,对于硫糖环素,一种新的非酶生物合成途径.
- 这项工作为了解和生产复杂的含硫天然产品开辟了新的途径.
更多相关视频
09:10Synthesis of Masarimycin, a Small Molecule Inhibitor of Gram-Positive Bacterial Growth
Published on: January 7, 2022
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
相关概念视频
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Nitriles to Ketones: Grignard Reaction
The mechanism begins with a nucleophilic attack by the Grignard...
Esters to Alcohols: Grignard Reaction
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
