Related Experiment Video
Updated: Jun 15, 2026

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
Published on: June 20, 2014
A stereoselective synthesis of alpha-deuterium-labelled (S)-alpha-amino acids
Elaine O'Reilly1, Daniele Balducci, Francesca Paradisi
1UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Belfield, Dublin 4, Ireland.
Abstract:
An atom-efficient and stereoselective synthesis has been developed for the preparation of alpha-2H-labelled (S)-alpha-amino acids, starting from a novel chiral diketopiperazine scaffold. Efficient mono-alkylation of the chiral template afforded the (S)-substituted adducts with the nature of the electrophile significantly effecting the stereochemical outcome. Subsequent alkylation was totally selective producing the 1,4-cis adduct as the sole diastereoisomer. The deprotection was carried out using cerium ammonium nitrate followed by acid hydrolysis affording the enantipure alpha-amino acids.
More Related Videos
08:40Millisecond Hydrogen/Deuterium-Exchange Mass Spectrometry for the Study of Alpha-Synuclein Structural Dynamics Under Physiological Conditions
Published on: June 23, 2022
07:26Metabolic Pathway Confirmation and Discovery Through 13C-labeling of Proteinogenic Amino Acids
Published on: January 26, 2012
Related Concept Videos
¹H NMR of Labile Protons: Deuterium (²H) Substitution
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
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...
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction