Related Experiment Video
Updated: Jul 3, 2026
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Serine Octamer Substitution Reactions With α-Hydroxy Acids
Keerthana Unni1,2, Brison A Shira1, Dylan T Holden1
1Department of Chemistry, Purdue University, West Lafayette, Indiana, USA.
Rationale:
The amino acid serine forms chiral magic number clusters, which can be studied using mass spectrometry (MS). Serine octamer clusters are also known to incorporate one or two nonserine monomers with serine monomers to make up the octamer.
Methods:
A Thermo LTQ ion trap mass spectrometer with nanoelectrospray ionization (nESI) was used to study cluster formation by both kinetically and energy-resolved methods. This study validates past observations on the homochiral preference of serine octamer during its association with other nonserine monomers.
Results:
A substrate scope covering α-hydroxy acids and related molecules was studied. The chiral preference was investigated with tandem MS and the importance of salt bridge formation and α/β-carbon hydrogen bonding was recognized.
Conclusions:
Weak interactions involving steric forces, salt bridges, ion-dipole interactions, and hydrogen bonds control stereoselective and chiroselective properties of the serine octamer cluster.
Related Concept Videos
01:17Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
01:01Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
01:38Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
00:51Base-Promoted α-Halogenation of Aldehydes and Ketones
01:28Amides to Carboxylic Acids: Hydrolysis
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
01:33Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes