PyAOP ((7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis.[1] It can be prepared from 1-hydroxy-7-azabenzotriazole (HOAt) and a chlorophosphonium reagent under basic conditions.[2] It is a derivative of the HOAt family of amide bond forming reagents. It is preferred over HATU, because it does not engage in side reactions with the N-terminus of the peptide.[3] Compared to the HOBt-containing analog PyBOP, PyAOP is more reactive due to the additional nitrogen in the fused pyridine ring of the HOAt moiety.[4] Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyAOP is potentially explosive.[5]
See also
BearbeitenEinzelnachweise
Bearbeiten- ↑ Tarek S. Mansour, Sujata Bardhan, Zhao-Kui Wan: Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications. In: Synlett. 2010. Jahrgang, Nr. 08, 2010, ISSN 0936-5214, S. 1143–1169, doi:10.1055/s-0029-1219820 (englisch, thieme-connect.de).
- ↑ Frank Hoffmann, Lothar Jäger, Carola Griehl: Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation. In: Phosphorus, Sulfur, and Silicon and the Related Elements. 178. Jahrgang, Nr. 2, 1. Februar 2003, ISSN 1042-6507, S. 299–309, doi:10.1080/10426500307942 (englisch, tandfonline.com).
- ↑ F. Albericio, M. Cases, J. Alsina, S. A. Triolo, L. A Carpino, S. Kates: On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis. In: Tetrahedron Letters. 38. Jahrgang, Nr. 27, 1997, S. 4853–4856, doi:10.1016/S0040-4039(97)01011-3.
- ↑ Albericio, Fernando, Bofill, Josep M., El-Faham, Ayman, Kates, Steven A.: Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1. In: The Journal of Organic Chemistry. 63. Jahrgang, Nr. 26. American Chemical Society, 1998, ISSN 0022-3263, S. 9678–9683, doi:10.1021/jo980807y.
- ↑ Jeffrey B. Sperry, Christopher J. Minteer, JingYa Tao, Rebecca Johnson, Remzi Duzguner, Michael Hawksworth, Samantha Oke, Paul F. Richardson, Richard Barnhart, David R. Bill, Robert A. Giusto, John D. Weaver: Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing. In: Organic Process Research & Development. 22. Jahrgang, Nr. 9, 21. September 2018, ISSN 1083-6160, S. 1262–1275, doi:10.1021/acs.oprd.8b00193 (englisch, acs.org).
[[Category:Hexafluorophosphates]] [[Category:Peptide coupling reagents]] [[Category:Triazolopyridines]] [[Category:Reagents for biochemistry]] [[Category:Quaternary phosphonium compounds]] [[Category:Organophosphorus compounds]]