92250-72-1

Upstream product

• 110-91-8 morpholine 
• 620151-96-4 (S)-ethyl N-(2-phenylcyclopropanecarbonyl)-4,4-dimethylpyroglutamate 
• 100-42-5 styrene 
• 939-87-7 2-phenyl-1-cyclopropanecarbonyl chloride 

Relevant academic research and scientific papers

Interfacing Microbial Styrene Production with a Biocompatible Cyclopropanation Reaction

Abstract The introduction of new reactivity into living organisms is a major challenge in synthetic biology. Despite an increasing interest in both the development of small-molecule catalysts that are compatible with aqueous media and the engineering of enzymes to perform new chemistry in vitro, the integration of non-native reactivity into metabolic pathways for small-molecule production has been underexplored. Herein we report a biocompatible iron(III) phthalocyanine catalyst capable of efficient olefin cyclopropanation in the presence of a living microorganism. By interfacing this catalyst with E.coli engineered to produce styrene, we synthesized non-natural phenyl cyclopropanes directly from D-glucose in single-vessel fermentations. This process is the first example of the combination of nonbiological carbene-transfer reactivity with cellular metabolism for small-molecule production.

Chemoselective Nucleophilic Attack on N-Acyl Derivatives of (S)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)

(Matrix presented) Heteronucleophiles and C-nucleophiles chemoselectively react with N-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of β-hydroxy acids likely by formation and ring opening of the corresponding β-lactones.