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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).
Coupling reagents (e.g. HBTU, HATU, or DIC) are employed to help form the peptide bond. The final deprotection is followed by a cleavage . The established method for the production of synthetic peptides in the lab is known as solid phase peptide synthesis (SPPS). [ 2 ]
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]
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
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).
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.
This reductive coupling can be viewed as involving two steps. First is the formation of a pinacolate (1,2- diolate ) complex, a step which is equivalent to the pinacol coupling reaction . The second step is the deoxygenation of the pinacolate, which yields the alkene , this second step exploits the oxophilicity of titanium.