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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 is commonly encountered in amine acylation reactions (i.e., amide formation). Such reactions are typically 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 (amine) to the active ester solution to afford the acylated product.
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]
Hydroxybenzotriazole (abbreviated HOBt) is an organic compound that is a derivative of benzotriazole.It is a white crystalline powder, which as a commercial product contains some water (~11.7% wt as the HOBt monohydrate crystal).
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]
This page was last edited on 15 December 2011, at 20:17 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
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
PBM coupling to synthesize aryl glycine. Racemic Clopidogrel, an antiplatelet agent, was synthesized in two steps using Petasis reaction. [18] synthesis of clopidogrel via PBM coupling. The Petasis reaction exhibits high degrees of stereocontrol when a chiral amine or aldehyde is used as a substrate.