Work

Synthesis of β-Deuterated Amino Acids via Palladium-Catalyzed H/D Exchange

Year: 2022

Type: article

Abstract: Despite several synthetic approaches that have been developed for α-deuterated amino acids, the synthesis of β-deuterated amino acids has remained a challenge. Herein, we disclose a palladium catalyzed H/D exchange protocol for a β-deuterated N-protected amino amide, which can be converted to a β-deuterated amino acid simply by removal of protecting groups. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of many amino amides. In addition, deuterium labeling of phenylalanine derivatives was also successful when pivalic acid served as an additive to promote the H/D exchange process.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.2c01654

Authors: Fei-Fei Sheng, Jian-Guo Gu, Kai-Hui Liu, Hong-Hai Zhang

Institutions: Nanjing Tech University, The Synergetic Innovation Center for Advanced Materials

Language: English

Topic: Chemical Reactions and Isotopes

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green