HATU

Short Summary : used in peptide coupling chemistry

Category : Amino Acids & Building Blocks|Peptide Coupling Reagents

Purity : 0.98

CAS Number : 148893-10-1

Formula : C10H15F6N6OP

Molecular Weight : 380.2

SMILE : CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F

Solubility : >16mg/mL in DMSO

Storage : Desiccate at -20°C

Description : HATU(1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) is a reagent used inpeptide couplingchemistry to generate an active ester from a carboxylic acid. HATU can be used along with Hnig’s base(N,N-diisopropylethylamine, DIPEA) to form amide bonds. The general solvent is DMF [1]. HATU has been commonly used in alcohol and amine acylation reactions such as amide and ester formation. Such reactions are commonly 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 to the active ester solution to form the acylated product such as alcohol or amine [2, 3].References:[1]. Carpino L A. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive[J]. Journal of the American Chemical Society, 1993, 115(10): 4397-4398.[2]. Carpino L A, Imazumi H, ElFaham A, et al. The uronium/guanidinium peptide coupling reagents: Finally the true uroniumsalts[J]. AngewandteChemie International Edition, 2002, 41(3): 441-445.[3]. Carpino L A, Imazumi H, Foxman B M, et al. Comparison of the Effects of 5-and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4-and 7-Isomers[J]. Organic letters, 2000, 2(15): 2253-2256.

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