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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
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 (Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium) 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), or triethylamine to form amide bonds. Typically DMF is used as solvent, although other polar aprotic solvents can ...
N,N ′-Diisopropylcarbodiimide is a carbodiimide used in peptide synthesis. [1] [2] As a liquid, it is easier to handle than the commonly used N,N ′-dicyclohexylcarbodiimide, a waxy solid. In addition, N,N ′-diisopropylurea, its byproduct in many chemical reactions, is soluble in most organic solvents, a property that facilitates work-up.
N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) [1] is an organic compound with the chemical formula (C 6 H 11 N) 2 C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis.
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]
BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) is a reagent commonly used for the synthesis of amides from carboxylic acids and amines in peptide synthesis. [ 1 ] [ 2 ] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. [ 3 ]
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]