Misplaced Pages

PyAOP reagent

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
PyAOP reagent
Names
IUPAC name (7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Other names PyAOP
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.575 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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;-1Key: CBZAHNDHLWAZQC-UHFFFAOYSA-N
SMILES
  • C1CCN(C1)(N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F(F)(F)(F)(F)F
Properties
Chemical formula C17H27F6N7OP2
Molar mass 521.389 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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. It can be prepared from 1-hydroxy-7-azabenzotriazole (HOAt) and a chlorophosphonium reagent under basic conditions. 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. 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. Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyAOP is potentially explosive.

See also

References

  1. Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications". Synlett. 2010 (08): 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.
Stub icon

This article about an organic compound is a stub. You can help Misplaced Pages by expanding it.

Categories: