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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Initiating polyketide biosynthesis by on-line methyl esterification.

Pengwei Li1, Meng Chen1,2, Wei Tang1,2

  • 1State Key Laboratory of Microbial Resources & CAS Key Laboratory of Microbial Physiological and Metabolic Engineering, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China.

Nature Communications
|July 24, 2021
PubMed
Summary

Aurantinins (ARTs) are antibacterial polyketides. A novel protecting group strategy using methyl esterification was discovered, preventing toxic intermediates and enabling active compound formation.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Natural Product Biosynthesis

Background:

  • Aurantinins (ARTs) are antibacterial polyketides with a complex fused tetracyclic structure.
  • Understanding the biosynthesis of ARTs is crucial for developing new antibiotics.

Purpose of the Study:

  • To identify the gene cluster responsible for ART biosynthesis.
  • To elucidate the C-methyl incorporation patterns and unique initiation strategy in ART production.
  • To investigate the role of methyltransferase Art28 and hydrolase Art9.

Main Methods:

  • Gene cluster identification and analysis.
  • Biochemical characterization of methyltransferase Art28 and hydrolase Art9.
  • Investigation of C-methyl incorporation patterns using biosynthetic studies.

Main Results:

  • The 'art' gene cluster was identified.
  • Art28 was characterized as a malonyl-acyl carrier protein O-methyltransferase, initiating biosynthesis via methyl esterification.
  • Art9 hydrolyzes the methyl ester, converting inactive ART 9B to active ART B, revealing a protecting group strategy.
  • This strategy is conserved across various bacteria.

Conclusions:

  • A novel on-line methyl esterification strategy initiates polyketide biosynthesis, acting as a protecting group.
  • This mechanism prevents unwanted side reactions and protects producing organisms from toxic intermediates.
  • The findings provide insights into polyketide biosynthesis and offer potential targets for antibiotic development.