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.
| Original language | English |
|---|---|
| Pages (from-to) | 16084-16089 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 87 |
| Issue number | 23 |
| DOIs | |
| State | Published - Dec 2 2022 |
| Externally published | Yes |
Funding
Part of this work was conducted at the Center for Nanophase Materials Sciences, which is a DOE Office of Science User Facility. Dr. Hong-Hai Zhang is currently supported by the Center for Structural Molecular Biology, sponsored by the Office of Biological and Environmental Research. This research was started by Hong-Hai Zhang as professor at Nanjing Tech University and completed at ORNL. We acknowledge the comments on the manuscript from Dr. Hugh M. O’Neil from ORNL. We acknowledge the National Natural Science Foundation of China (Grant Number 22075135).