Peptides & Peptide Synthesis Products

PyAOP

PyAOP

$47.00
$47.00
PyAOP, Catalog No: 31007
High Purity >99%, (7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, CAS: 156311-83-0, MW: 521.38, Formula: C17H27F6N7OP2
Catalog No: 31007
High Purity >99%, (7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, CAS: 156311-83-0, MW: 521.38, Formula: C17H27F6N7OP2

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PyAOP >99% Pure ((7-Azabenzotriazol-1-yloxy)tripyr-rolidinophosphonium hexafluorophosphate)

This coupling agent is a derivative of the HOAt family useful in preparing a range of difficult peptides especially amino acids of a hindered nature. An advantage of this uronium salt is that it can be used in greater excesses and does not under go dertimental side reactions at the amino terminus which blocks further assembly of a Fmoc amino acids(1.).

The pyrrolidino derivatives appear to be the reagent of choice relative to the piperidino compounds or those formed from trialkylamines. Further it has been determined that the various other aminium/onium salts (HOAt and HOBt) should be used for the activation of hindered species, since the latter may lead to the formation of guanidino derivatives (2.).

1. Fernando Albericio, Marta Cases, Jordi Alsina, Salvadore Triolo, Louis Carpino and Steven Kates. Tetrahedron Letters, Volume 38, Issue 27, 7 July 1997 Pages 4853-4856.
2. Fernando Albericio, Josep Bofill. Ayman El-Faham and Steven Kates, J. Org Chem. 1998; 63(26) pp 978-9683. The Journal of Organic Chemistry, 1998, 63 (26) Pages 9678-9683.

Additional Information

Additional Information

Catalog Number 31007
CAS 156311-83-0
M.W. 521.38
Formula C17H27F6N7OP2
IUPAC Name tripyrrolidin-1-yl(triazolo[4,5-b]pyridin-3-yloxy)phosphanium hexafluorophosphate
Synonym (7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Also Known As
  • tripyrrolidin-1-yl-(triazolo[5,4-b]pyridin-3-yloxy)phosphanium hexafluorophosphate
  • tripyrrolidin-1-yl-(triazolo[5,4-b]pyridin-3-yloxy)phosphonium hexafluorophosphate
  • tri1-pyrrolidinyl-(3-triazolo[5,4-b]pyridinyloxy)phosphonium hexafluorophosphate
  • tripyrrolidin-1-yl-([1,2,3]triazolo[5,4-b]pyridin-3-yloxy)phosphanium hexafluorophosphate
InChIKey CBZAHNDHLWAZQC-UHFFFAOYSA-N
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
SMILES C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
Cited Uses

Details

1. Chang YS et al, "Stapled ?-helical peptide drug development: A potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy", Proceedings of the National Academy of Sciences of the United States of America, 110(36) pp.E3445-E3454 (2013 Sep 3).
2. Chen M et al, "Mechanistic Insights from the Binding of Substrate and Carbocation Intermediate Analogues to Aristolochene Synthase", Biochemistry, 52(32) pp.5441-5453 (2013 Aug 13).
3. Shirazi AN et al, "Surface Decorated Gold Nanoparticles by Linear and Cyclic Peptides as Molecular Transporters", Molecular pharmaceutics, 10(8) pp.10.1021/mp400199e (2013 Aug 5).
4. Pelay-Gimeno M et al, "Head-to-Side-Chain Cyclodepsipeptides of Marine Origin", Marine Drugs, 11(5) pp.1693-1717 ().
5. Banappagari S et al, "Design, synthesis and characterization of peptidomimetic conjugate of BODIPY targeting HER2 protein extracellular domain", European journal of medicinal chemistry, 65() pp.60-69 (2013 Jul).
6. Knerr PJ et al, "Chemical Synthesis of the Lantibiotic Lacticin 481 Reveals the Importance of Lanthionine Stereochemistry", Journal of the American Chemical Society, 135(19) pp.7094-7097 (2013 May 15).
7. Shirazi AN et al, "Efficient Delivery of Cell Impermeable Phosphopeptides by a Cyclic Peptide Amphiphile Containing Tryptophan and Arginine", Molecular pharmaceutics, 10(5) pp.2008-2020 (2013 May 6).
8. Alley WR Jr et al, "Structural Glycomic Analyses at High Sensitivity: A Decade of Progress", Annual review of analytical chemistry (Palo Alto, Calif.), 6() pp.237-265 (2013).
9. Alley WR Jr et al, "High-sensitivity Analytical Approaches for the Structural Characterization of Glycoproteins", Chemical reviews, 113(4) pp.2668-2732 (2013 Apr 10).
10. Li Y et al, "Direct detection of collagenous proteins by fluorescently labeled collagen mimetic peptides", Bioconjugate chemistry, 24(1) pp.9-16 (2013 Jan 16).
11. Stahl PJ et al, "Encoding Cell-Instructive Cues to PEG-Based Hydrogels via Triple Helical Peptide Assembly", Soft matter, 8() pp.10409-10418 (2012 Jan 1).
12. Wang PS et al, "Relationship between side-chain branching and stoichiometry in ?3-peptide bundles", Tetrahedron, 68(23) pp.4342-4345 (2012 Jun 10).
13. Puckett JW et al, "Microwave Assisted Synthesis of Py-Im Polyamides", Organic Letters, 14(11) pp.2774-2777 (2012 Jun 1).
14. Knerr PJ et al, "Chemical Synthesis and Biological Activity of Analogues of the Lantibiotic Epilancin 15X", Journal of the American Chemical Society, 134(18) pp.7648-7651 (2012 May 9).
15. Prats-Alfonso E et al, "Cancer Prognostics by Direct Detection of p53-Antibodies on Gold Surfaces by Impedance Measurements", Small (Weinheim an der Bergstrasse, Germany), 8(13) pp.2106-2115 (2012 Jul 9).
16. Nie H et al, "Recent Advances in Sialic Acid-Focused Glycomics", Journal of Proteomics, 75(11) pp.3098-3112 (2012 Jun 18).
17. Garcia JM et al, "Total Synthesis of Nominal (11S)- and (11R)-Cyclocinamide A", Organic Letters, 14(8) pp.2054-2057 (2012 Apr 20).
18. Simpson LS et al, "A Cleavable Scaffold Strategy for the Synthesis of One-Bead One-Compound Cyclic Peptoid Libraries That Can Be Sequenced By Tandem Mass Spectrometry", Tetrahedron letters, 53(18) pp.2341-2344 (2012 May 2).
19. Stahl PJ et al, "On-the-Resin N-Terminal Modification of Long Synthetic Peptides", Analytical Biochemistry, 424(2) pp.137-139 (2012 May 15).
20. Seiple IB et al, "Enantioselective Total Syntheses of (-)-Palau'amine, (-)- Axinellamines, and (-)-Massadines", Journal of the American Chemical Society, 133(37) pp.14710-14726 (2011 Sep 21).
21. Aggarwal S et al, "[DLys6]-LHRH-Curcumin Conjugate Inhibits Pancreatic Cancer Cell Growth in vitro and in vivo", International journal of cancer. Journal international du cancer, 129(7) pp.1611-1623 (2011 Oct 1).
22. Krusemark CJ et al, "Complete chemical modification of amine and acid functional groups of peptides and small proteins", Methods in molecular biology (Clifton, N.J.), 753() pp.10.1007/978-1-61779-148-2_6 (2011).
23. Kokatla HP et al, "One-Pot Etherification of Purine Nucleosides and Pyrimidines", Organic letters, 12(20) pp.4478-4481 (2010 Oct 15).
24. Lassen KM et al, "An efficient synthesis of the tamandarin B macrocycle", Tetrahedron letters, 51(13) pp.1635-1638 (2010 Mar 31).
25. Castilla AM et al, "Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides", Beilstein Journal of Organic Chemistry, 6() pp.5 ().
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