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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).
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.
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]
In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst .
Phosphonium reagents include BOP (HOBt), PyBOP (HOBt) and PyAOP (HOAt). [18] Although these reagents can lead to the same activated ester intermediates as a carbodiimide reagent, the rate of activation is higher due to the high electrophilicty of these cationic reagents. [ 19 ]
1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole used as a peptide coupling reagent. [2] It suppresses racemization that can otherwise occur during the reaction. [3] HOAt has a melting point of 213-216 °C. [4]
PyAOP ((7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. [1] It can be prepared from 1-hydroxy-7-azabenzotriazole (HOAt) and a chlorophosphonium reagent under basic conditions. [ 2 ]
or the coupling reagent COMU which is readily soluble as a dimethylmorpholine-uronium salt and which, like Oxyma, is superior to the standard additive HOBt for the suppression of racemization and acylation efficiency and is comparable to HOAt without presenting an explosion risk such as the benzotriazoles. [5]