Work

Biocatalytic, Stereoselective Deuteration of α‑Amino Acids and Methyl Esters

Year: 2020

Type: article

Abstract: α-2H Amino acids are valuable precursors toward labeled pharmaceutical agents and tools for studying biological systems; however, these molecules are costly to purchase and challenging to synthesize in a site- and stereoselective manner. Here, we show that an α-oxoamine synthase that evolved for saxitoxin biosynthesis, SxtA AONS, is capable of producing a range of α-2H amino acids and esters site- and stereoselectively using D2O as the deuterium source. Additionally, we demonstrate the utility of this operationally simple reaction on preparative-scale in the stereoselective chemoenzymatic synthesis of a deuterated analogue of safinamide, a drug used to treat Parkinson’s disease.

Source: ACS Catalysis

DOI: 10.1021/acscatal.0c01885

Authors: Stephanie W. Chun, Alison R. H. Narayan

Institution: University of Michigan

Language: English

Topic: Chemical Reactions and Isotopes

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Expanding the synthetic utility of enzymes