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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal,...

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

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Preparation and Use of Samarium Diiodide SmI2 in Organic Synthesis: The Mechanistic Role of HMPA and NiII Salts in the Samarium Barbier Reaction

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Efficient Transferase Engineering for SAM Analog Synthesis from Iodoalkanes.

Kai H Schülke¹, Jana S Fröse¹, Alina Klein¹

¹Organic Chemistry and Biocatalysis, Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615, Bielefeld, Germany.

Chembiochem : a European Journal of Chemical Biology

|March 13, 2024

Summary

Researchers engineered enzymes to create novel S-Adenosyl-l-methionine (SAM) analogs from simple reagents. This breakthrough expands biocatalytic alkylation chemistry using readily available starting materials.

Keywords:

Biocatalysis Enzyme engineering Methyltransferases SAM analogs

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Published on: January 15, 2018

Area of Science:

Biocatalysis
Enzyme Engineering
Organic Chemistry

Background:

S-Adenosyl-l-methionine (SAM) is crucial for methyl transfer reactions.
Expanding SAM analog chemistry requires efficient regeneration methods.

Purpose of the Study:

Develop an enzyme engineering strategy for synthesizing diverse SAM analogs.
Enable SAM analog regeneration using accessible iodoalkanes.

Main Methods:

Simultaneous mutation of hydrophobic and dynamic amino acids in SAM-dependent enzymes.
Combinatorial mutagenesis guided by natural amino acid diversity.
High-throughput chromatographic screening for SAM analog analysis.

Main Results:

Generated a library of highly functional enzyme mutants with significantly increased activity.
Optimized enzymes exhibit high catalytic efficiencies (up to 31 M⁻¹s⁻¹) and stereoselectivity (>99% de).
Enzymes successfully converted various iodoalkanes, including cyclopropyl and aromatic moieties.

Conclusions:

The developed enzyme engineering strategy efficiently produces SAM analogs.
This approach advances selective biocatalytic alkylation chemistry.
Enables SAM analog regeneration with readily available reagents.