HATU

• CAT Number: R012398
• CAS Number: 148893-10-1
• Molecular Formula: C10H15F6N6OP
• Molecular Weight: 380.24
• Purity: ≥95%
• Synonyms: 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-Oxide Hexafluorophosphate
• Storage: -20°C
• Related CAS: 17112-07-1 164298-23-1 1513-66-2 174669-74-0
• IUPAC Name: [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium;hexafluorophosphate
• InChI: InChI=1S/C10H15N6O.F6P/c1-13(2)10(14(3)4)15-8-6-5-7-11-9(8)16(17)12-15;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
• InChIKey: FKBFHOSFPRWJNV-UHFFFAOYSA-N
• SMILES: CN(C)C(=[N+](C)C)N1C2=C(N=CC=C2)[N+](=N1)[O-].F[P-](F)(F)(F)(F)F

HATU (Cat No.:R012398) is a highly efficient coupling reagent widely used in peptide synthesis and organic chemistry. It facilitates the formation of amide bonds between carboxylic acids and amines with minimal racemization. HATU is particularly favored in solid-phase peptide synthesis (SPPS) for its rapid reaction rates and high yields. The presence of the 7-azabenzotriazole leaving group enhances the reactivity and solubility of the activated intermediates. HATU is commonly used with bases like DIPEA or NMM and is essential in the preparation of complex peptides, pharmaceutical intermediates, and other amide-containing molecules.

Reference

1:Evaluation of combined use of Oxyma and HATU in aggregating peptide sequences. Caporale A, Doti N, Sandomenico A, Ruvo M.J Pept Sci. 2017 Apr;23(4):272-281. doi: 10.1002/psc.2977. Epub 2017 Jan 31. PMID: 28139012
2:Mineral resources prospecting by synthetic application of TM/ETM+, Quickbird and Hyperion data in the Hatu area, West Junggar, Xinjiang, China. Liu L, Zhou J, Jiang D, Zhuang D, Mansaray LR, Hu Z, Ji Z.Sci Rep. 2016 Feb 25;6:21851. doi: 10.1038/srep21851. PMID: 26911195 Free PMC Article
3:Peptide bond-forming reagents HOAt and HATU are not mutagenic in the bacterial reverse mutation test. Nicolette J, Neft RE, Vanosdol J, Murray J.Environ Mol Mutagen. 2016 Apr;57(3):236-40. doi: 10.1002/em.21997. Epub 2016 Feb 3. PMID: 26840011
4:Rapid HATU-mediated solution phase siRNA conjugation. Aaronson JG, Klein LJ, Momose AA, O/'Brien AM, Shaw AW, Tucker TJ, Yuan Y, Tellers DM.Bioconjug Chem. 2011 Aug 17;22(8):1723-8. doi: 10.1021/bc2001227. Epub 2011 Jul 11. PMID: 21744777
5:Supramolecular motifs in the first structures of organic carboxylate salts of 1-(diaminomethylene)thiourea (HATU). Hołyńska M, Kubiak M.Acta Crystallogr C. 2009 Aug;65(Pt 8):o410-3. doi: 10.1107/S0108270109026390. Epub 2009 Jul 15. PMID: 19652326
6:Synthesis of 3-substituted-4(3H)-quinazolinones via HATU-mediated coupling of 4-hydroxyquinazolines with amines. Xiao Z, Yang MG, Li P, Carter PH.Org Lett. 2009 Mar 19;11(6):1421-4. doi: 10.1021/ol802946p. PMID: 19243133
7:Occupational contact urticaria from the solid-phase peptide synthesis coupling agents HATU and HBTU. Yung A, Papworth-Smith J, Wilkinson SM.Contact Dermatitis. 2003 Aug;49(2):108-9. No abstract available. PMID: 14641366