HATU

  • CAT Number: R012398
  • CAS Number: 148893-10-1
  • Molecular Formula: C10H15F6N6OP
  • Molecular Weight: 380.235
  • Purity: ≥95%
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HATU (CAS 148893-10-1; 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid. HATU is used along with Hünig/'s base (N,N-diisopropylethylamine, DIPEA) to form amide bonds. Generally DMF is used as solvent, although other polar organic solvents can also be used. (Source: https://en.wikipedia.org/wiki/HATU).

Catalog Number R012398
CAS Number 148893-10-1
Synonyms

1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-Oxide Hexafluorophosphate;

Molecular Formula

C10H15F6N6OP

Purity 95%
Storage -20°C
IUPAC Name [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium;hexafluorophosphate
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
InChIKey JNWBBCNCSMBKNE-UHFFFAOYSA-N
SMILES CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
Reference

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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<br />
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<br />
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<br />
4:Rapid HATU-mediated solution phase siRNA conjugation. Aaronson JG, Klein LJ, Momose AA, O/&#39;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<br />
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<br />
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<br />
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

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