PyAOP reagent

PyAOP ((7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) is a coupling reagent used in solid phase peptide synthesis. It is a derivative of the HOAt family of coupling reagents. It is preferred over HATU, because it does not side react at the N-terminus of the peptide.[1] Compared to the HOBt derivates, PyAOP (and HOAt in general) are more reactive due to the additional nitrogen.[2]

PyAOP reagent
Names
IUPAC name
(7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Other names
PyAOP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.575
  • InChI=1S/C17H27N7OP.F6P/c1-2-11-21(10-1)26(22-12-3-4-13-22,23-14-5-6-15-23)25-24-17-16(19-20-24)8-7-9-18-17;1-7(2,3,4,5)6/h7-9H,1-6,10-15H2;/q+1;-1
    Key: CBZAHNDHLWAZQC-UHFFFAOYSA-N
  • C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
Properties
C17H27F6N7OP2
Molar mass 521.389 g·mol−1
Appearance White crystals
Melting point 163–168 °C (325–334 °F; 436–441 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Albericio, F.; Cases, M.; Alsina, J.; Triolo, S. A.; Carpino, L. A; Kates, S. (1997). "On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis". Tetrahedron Letters. 38 (27): 4853–4856. doi:10.1016/S0040-4039(97)01011-3.
  2. Albericio, Fernando; Bofill, Josep M.; El-Faham, Ayman; Kates, Steven A. (1998). "Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1". The Journal of Organic Chemistry. American Chemical Society. 63 (26): 9678–9683. doi:10.1021/jo980807y. ISSN 0022-3263.
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