PyAOP reagent explained

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

Notes and References

  1. Mansour . Tarek S. . Bardhan . Sujata . Wan . Zhao-Kui . 2010 . Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications . Synlett . en . 2010 . 08 . 1143–1169 . 10.1055/s-0029-1219820 . 0936-5214.
  2. Hoffmann . Frank . Jäger . Lothar . Griehl . Carola . 2003-02-01 . Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation . Phosphorus, Sulfur, and Silicon and the Related Elements . en . 178 . 2 . 299–309 . 10.1080/10426500307942 . 1042-6507.
  3. 10.1016/S0040-4039(97)01011-3 . On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis . 1997 . Albericio. F. . Cases. M. . Alsina . J. . Triolo . S. A. . Carpino . L. A . Kates . S. . Tetrahedron Letters . 38 . 27 . 4853–4856.
  4. Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1. Albericio, Fernando. Bofill, Josep M.. El-Faham, Ayman. Kates, Steven A.. 1998. The Journal of Organic Chemistry. 9678–9683. 63. 26. American Chemical Society. 0022-3263. 10.1021/jo980807y.
  5. Sperry . Jeffrey B. . Minteer . Christopher J. . Tao . JingYa . Johnson . Rebecca . Duzguner . Remzi . Hawksworth . Michael . Oke . Samantha . Richardson . Paul F. . Barnhart . Richard . Bill . David R. . Giusto . Robert A. . Weaver . John D. . 2018-09-21 . Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing . Organic Process Research & Development . en . 22 . 9 . 1262–1275 . 10.1021/acs.oprd.8b00193 . 1083-6160.

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