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Highly Selective Directed Iridium‐Catalyzed Hydrogen Isotope Exchange Reactions of Aliphatic Amides
| Content Provider | Semantic Scholar |
|---|---|
| Author | Valero, Mégane Weck, Remo Güssregen, Stefan Atzrodt, Jens Derdau, Volker |
| Copyright Year | 2018 |
| Abstract | For the first time, we describe highly selective homogeneous iridium-catalyzed hydrogen isotope exchange (HIE) of unactivated C(sp3 ) centers in aliphatic amides. When using the commercially available Kerr catalyst, the HIE with a series of common antibody-drug conjugate (ADC) linker side chains proceeds with high yields, high regioselectivity, and with deuterium incorporation up to 99 %. The method is fully translatable to the specific requirements of tritium chemistry and its effectiveness was demonstrated by direct tritium labelling of a maytansinoid. The scope of the method can be extended to simple amino acids, with high HIE activity observed for glycine and alanine. In di- and tripeptides, a very interesting protecting-group-dependent tunable selectivity was observed. DFT calculations gave insight into the energies of the transition states, thereby explaining the observed selectivity and the influence of the amino acid protecting groups. |
| Starting Page | 8159 |
| Ending Page | 8163 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| PubMed reference number | 29693316v1 |
| Alternate Webpage(s) | https://doi.org/10.1002/anie.201804010 |
| DOI | 10.1002/anie.201804010 |
| Journal | Angewandte Chemie |
| Volume Number | 57 |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | Alanine Amino Acids Deuterium Energy, Physics Glycine Hydrogen Peroxide 30 MG/ML Topical Solution Hypoxic-Ischemic Encephalopathy Iridium Isotopes Ninety Nine Tritium |
| Content Type | Text |
| Resource Type | Article |
