A mechanochemical approach to access the proline–proline diketopiperazine framework
Copyright policy )A mechanochemical approach to access the proline–proline diketopiperazine framework
Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline–proline dipeptides under solvent-free conditions. A deprotection–cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro–Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.
Pharmacology, Toxicology and Pharmaceutics, Nucleophile, Proline, Science, pyrrolidine, Organic chemistry, Combinatorial chemistry, Diketopiperazines, DFT calculations, Toxicology, Protein Engineering, Biochemistry, Full Research Paper, Catalysis, Enantioselective synthesis, QD241-441, Chemical engineering, Engineering, Stereochemistry, Biochemistry, Genetics and Molecular Biology, Ball mill, Physical and Theoretical Chemistry, Cyclotide Bioengineering and Protein Anchoring Mechanisms, Molecular Biology, FOS: Chemical engineering, Noncovalent Interactions in Molecular Crystals and Supramolecular Chemistry, Q, diketopiperazine, Life Sciences, Stereoselectivity, ball mill, Amino acid, Chemistry, Role of Quinones in Toxicology and Pharmacology, Physical Sciences, Enantiopure drug, mechanochemistry
Pharmacology, Toxicology and Pharmaceutics, Nucleophile, Proline, Science, pyrrolidine, Organic chemistry, Combinatorial chemistry, Diketopiperazines, DFT calculations, Toxicology, Protein Engineering, Biochemistry, Full Research Paper, Catalysis, Enantioselective synthesis, QD241-441, Chemical engineering, Engineering, Stereochemistry, Biochemistry, Genetics and Molecular Biology, Ball mill, Physical and Theoretical Chemistry, Cyclotide Bioengineering and Protein Anchoring Mechanisms, Molecular Biology, FOS: Chemical engineering, Noncovalent Interactions in Molecular Crystals and Supramolecular Chemistry, Q, diketopiperazine, Life Sciences, Stereoselectivity, ball mill, Amino acid, Chemistry, Role of Quinones in Toxicology and Pharmacology, Physical Sciences, Enantiopure drug, mechanochemistry
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