2025-10-02 日本原子力研究機構,J-PARCセンター,総合科学研究機構
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アミノ酸の直接重水素化法の開発と重水素化トリプトファンの特性評価 Development of the Direct Deuteration Method for Amino Acids and Characterization of Deuterated Tryptophan
Chie Shibazaki,Haruki Sugiyama,Misaki Ueda,Takayuki Oku,Motoyasu Adachi,Zoë Fisher and Kazuhiro Akutsu-Suyama
Bioengineering Published: 16 September 2025
DOI:https://doi.org/10.3390/bioengineering12090981
Abstract
Proteins and peptides are vital biomolecules, and deuterated amino acids are increasingly applied in areas such as drug discovery, metabolic tracing, and neutron scattering studies. In this study, we performed deuteration on all 20 proteinogenic amino acids, including their side chains, and established efficient methods for 13 amino acids. Using a Pt/C-catalyzed hydrogen–deuterium exchange reaction, the reaction parameters were optimized to achieve the selective and stable incorporation of deuterium. In addition, the resulting deuterated compounds, focusing on tryptophan, were characterized in order to assess their physicochemical properties. Because the deuteration reaction caused significant racemization of amino acids, deuterated D/L-tryptophan was isolated using a chiral separation method. Deuterated tryptophan characterization studies confirmed that the photostability was markedly enhanced by deuteration, whereas the acid stability showed no clear isotopic effect. The X-ray crystal structure analyses revealed minimal changes upon the hydrogen-to-deuterium substitution. These results provide a robust platform for the supply of deuterated amino acids, facilitating their application in drug development, structural analysis, and creation of advanced functional biomaterials.
