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HATU
HATU (1-()-1H-1,2,3-triazolo()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.
==History==
HATU was first reported by Louis A. Carpino in 1993 as an efficient means of preparing active esters derived from 1-hydroxy-7-azabenzotriazole (HOAt).〔(Carpino, L. A., ''J. Am. Chem. Soc.'' 1993, 115 (10), 4397-4398. )〕 HATU can exist as either the uronium salt (''O-''form) or the less reactive iminium salt (''N''-form). HATU was initially reported as the O-form (1) using the original preparation reported by Carpino; however, X-ray crystallographic and NMR studies revealed the true structure of HATU to be the less reactive guanidinium isomer (2).〔(Carpino, L. A.; Imazumi, H.; El-Faham, A.; Ferrer, F. J.; Zhang, C.; Lee, Y.; Foxman, B. M.; Henklein, P.; Hanay, C.; Mügge, C.; Wenschuh, H.; Klose, J.; Beyermann, M.; Bienert, M., ''Angew. Chem. Intd. Ed.'' 2002, 41 (3), 441-445. )〕 It is, however, possible to obtain the uronium isomer by preparing HATU using KOAt in place of HOAt and working up the reaction mixture quickly to prevent isomerisation.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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