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HBTU (Hexafluorophosphate Benzotriazole Tetramethyl Uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. It was introduced in 1978 and shows resistance against racemization.
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). [2] HATU is commonly prepared from HOAt and TCFH under basic conditions [3] and can exist as either the uronium salt (O-form) or the less reactive iminium salt (N-form).
HCTU is an amidinium coupling reagent used in peptide synthesis.It is analogous to HBTU. [1] The HOBt moiety has a chlorine in the 6 position which improves reaction rates and the synthesis of difficult couplings [2] [3] HCTU and related reagents containing the 6-chloro-1-hydroxybenzotriazole moiety can be prepared by reaction with TCFH under basic conditions. [4]
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2011-05-20 22:10 AlexNB 453×194× (39518 bytes) Chemicl structures of several commonly used uronium-based peptide coupling reagents: HATU, HBTU, HCTU, COMU. Captions English
TCFH itself is a common reagent used in the preparation of uronium and guanidinium salts used for amide bond formation and peptide synthesis, such as HATU. [3] [4] [5]Amide bond formation with TCFH can be performed in a wide range of organic solvents, most commonly acetonitrile, but also water [6] and in the solid state. [7]