Peptides & Peptide Synthesis Products

HATU

HATU
$12.00
$12.00
HATU, Catalog No: 31006
O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, CAS: 148893-10-1, MW: 380.23, Formula: C10H15F6N6OP
Catalog No: 31006
O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, CAS: 148893-10-1, MW: 380.23, Formula: C10H15F6N6OP

* Required Fields

Description

Details

HATU

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

(1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate)

HATU is commonly encountered in alcohol and amine acylation reactions (i.e., ester and amide formation). Such reactions are typically performed in two distinct reaction steps: (1) reaction of a carboxylic acid with HATU to form the OAt-active ester; then (2) addition of the nucleophile (e.g., alcohol or amine) to the active ester solution to afford the acylated product.

In the first step, the carboxylate anion (formed by deprotonation by an organic base attacks HATU to form the unstable O-acyl(tetramethyl)isouronium salt. The OAt anion rapidly attacks the isouronium salt, affording the OAt-active ester and liberating a stoichiometric quantity of tetramethylurea. Addition of a nucleophile, such as an amine, to the OAt-active ester results in acylation. The solubility should be 1mM in 20mL of DMF.

Storage should be under refrigerated conditions until time of use.

1. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive J. Am. Chem. Soc., 1993, 115 (10), pp 4397–4398

Additional Information

Additional Information

Catalog Number 31006
CAS 148893-10-1
M.W. 380.23
Formula C10H15F6N6OP
IUPAC Name [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium hexafluorophosphate
Synonym O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
Also Known As
  • [dimethylamino-(triazolo[5,4-b]pyridin-3-yloxy)methylidene]-dimethylazanium hexafluorophosphate
  • [dimethylamino-(triazolo[5,4-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate
  • [dimethylamino-(3-triazolo[5,4-b]pyridinyloxy)methylene]-dimethylammonium hexafluorophosphate
  • [dimethylamino-([1,2,3]triazolo[5,4-b]pyridin-3-yloxy)methylidene]-dimethyl-azanium hexafluorophosphate
  • O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
  • 11373_FLUKA
  • HATU
  • N,N,N',N'-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate
  • O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
  • 445460_ALDRICH
InChIKey JNWBBCNCSMBKNE-UHFFFAOYSA-N
InChI InChI=1S/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
SMILES CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
Cited Uses

Details

1. Kopka K et al, "Pharmaceuticals--Special Issue on Radiopharmaceutical Chemistry between Imaging and Endoradiotherapy", Pharmaceuticals, 7(7) pp.839-849 ().
2. Willems MM et al, "Design, automated synthesis and immunological evaluation of NOD2-ligand-antigen conjugates", Beilstein Journal of Organic Chemistry, 10() pp.1445-1453 ().
3. Lepage ML et al, "Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores", Beilstein Journal of Organic Chemistry, 10() pp.1406-1412 ().
4. Wang J et al, "Investigation of Indolglyoxamide and Indolacetamide Analogues of Polyamines as Antimalarial and Antitrypanosomal Agents", Marine Drugs, 12(6) pp.3138-3160 ().
5. Fischer CA et al, "A Bombesin-Shepherdin Radioconjugate Designed for Combined Extra- and Intracellular Targeting", Pharmaceuticals, 7(6) pp.662-675 ().
6. Mäde V et al, "Automated solid-phase peptide synthesis to obtain therapeutic peptides", Beilstein Journal of Organic Chemistry, 10() pp.1197-1212 ().
7. Bhattacharyya T et al, "Development of Peptide-Based Lineage-Specific Serology for Chronic Chagas Disease: Geographical and Clinical Distribution of Epitope Recognition", PLoS Neglected Tropical Diseases, 8(5) pp.e2892 ().
8. Wong CT et al, "Realizing serine/threonine ligation: scope and limitations and mechanistic implication thereof", Frontiers in Chemistry, 2() pp.28 ().
9. Singh AN et al, "Dimerization of a Phage-Display Selected Peptide for Imaging of ?v?6- Integrin: Two Approaches to the Multivalent Effect", Theranostics, 4(7) pp.745-760 ().
10. Kojima A et al, "Prion Fragment Peptides Are Digested with Membrane Type Matrix Metalloproteinases and Acquire Enzyme Resistance through Cu2+-Binding", Biomolecules, 4(2) pp.510-526 ().
11. Mosquera J et al, "Selective DNA-Binding by Designed Bisbenzamidine-Homeodomain Chimeras", Chembiochem : a European journal of chemical biology, 15(8) pp.1092-1095 (2014 May 26).
12. Maschauer S et al, "In Vivo Monitoring of the Antiangiogenic Effect of Neurotensin Receptor-Mediated Radiotherapy by Small-Animal Positron Emission Tomography: A Pilot Study", Pharmaceuticals, 7(4) pp.464-481 ().
13. Amato F et al, "Exploitation of a Very Small Peptide Nucleic Acid as a New Inhibitor of miR-509-3p Involved in the Regulation of Cystic Fibrosis Disease-Gene Expression", BioMed Research International, 2014() pp.610718 (2014).
14. Manouilidou MD et al, "Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability", Beilstein Journal of Organic Chemistry, 10() pp.774-783 ().
15. Gaglione M et al, "Synthesis and Gene Silencing Properties of siRNAs Containing Terminal Amide Linkages", BioMed Research International, 2014() pp.901617 (2014).
16. Hatu G et al, "Lower ribavirin biodisponibility in patients with HIV-HCV coinfection in comparison with HCV monoinfected patients", BMC Infectious Diseases, 14() pp.150 ().
17. Behrends M et al, "N-Aryl Isoleucine Derivatives as Angiotensin II AT2 Receptor Ligands", ChemistryOpen, 3(2) pp.65-75 (2014 Apr).
18. Henriksen JR et al, "Side Chain Hydrophobicity Modulates Therapeutic Activity and Membrane Selectivity of Antimicrobial Peptide Mastoparan-X", PLoS ONE, 9(3) pp.e91007 ().
19. Browne L et al, "Imidazol-1-ylethylindazole Voltage-Gated Sodium Channel Ligands Are Neuroprotective during Optic Neuritis in a Mouse Model of Multiple Sclerosis", Journal of Medicinal Chemistry, 57(7) pp.2942-2952 (2014 Apr 10).
20. Koopmanschap G et al, "Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics", Beilstein Journal of Organic Chemistry, 10() pp.544-598 ().
21. Byzia A et al, "A remarkable activity of human leukotriene A4 hydrolase (LTA4H) toward unnatural amino acids", Amino Acids, 46() pp.1313-1320 (2014).
22. Murcia C et al, "Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf formosa. Isolation and Total Synthesis", Marine Drugs, 12(2) pp.1116-1130 ().
23. Creech GS et al, "Chemical synthesis of the ATAD2 bromodomain", Proceedings of the National Academy of Sciences of the United States of America, 111(8) pp.2891-2896 (2014 Feb 25).
24. Zhang Q et al, "Synthesis of granulocyte-macrophage colony-stimulating factor as homogeneous glycoforms and early comparisons with yeast cell-derived material", Proceedings of the National Academy of Sciences of the United States of America, 111(8) pp.2885-2890 (2014 Feb 25).
25. Forde É et al, "Potential of Host Defense Peptide Prodrugs as Neutrophil Elastase-Dependent Anti-Infective Agents for Cystic Fibrosis", Antimicrobial Agents and Chemotherapy, 58(2) pp.978-985 (2014 Feb).
Reviews
cr