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Updated: Jun 1, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis of histidinoalanine: a comparison of β-lactone and sulfamidate electrophiles
Carol M Taylor1, Samanthi Thabrew De Silva
1Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States. cmtaylor@lsu.edu
Abstract:
Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-β-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of τ- and π-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the τ-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared τ-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, τ-L-histidinyl-D-alanine (τ-4), as a salt-free standard for amino acid analysis.
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