PyAOP reagent

PyAOP reagent

Names
IUPAC name (7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Other names PyAOP
Identifiers
CAS Number	156311-83-0
3D model (JSmol)	Interactive image
ChemSpider	9213814  Y
ECHA InfoCard	100.155.575
PubChem CID	11038641
UNII	C5Z532MU8E  Y
CompTox Dashboard (EPA)	DTXSID00935424
InChI 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
SMILES C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
Properties
Chemical formula	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

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

• BOP reagent

References

1. Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications" . Synlett. 2010 (8): 1143–1169. doi:10.1055/s-0029-1219820. ISSN   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. 178 (2): 299–309. doi:10.1080/10426500307942. ISSN   1042-6507.
3. 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.
4. 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. 63 (26). American Chemical Society: 9678–9683. doi:10.1021/jo980807y. ISSN   0022-3263.
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. 22 (9): 1262–1275. doi:10.1021/acs.oprd.8b00193. ISSN   1083-6160.