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Biocatalytic, Stereoselective Deuteration of α-Amino Acids and Methyl Esters.

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-oxo-amine 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 analog of safinamide, a drug used to treat Parkinson's disease.

SUBMITTER: Chun SW

PROVIDER: S-EPMC8382264 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Biocatalytic, Stereoselective Deuteration of α-Amino Acids and Methyl Esters.

Chun Stephanie W SW Narayan Alison R H ARH

ACS catalysis 20200623 13

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-oxo-amine 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. Addition ...[more]

PMID: 34430066

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