Abstract

Publisher Summary This chapter discusses the use of novel coupling reagents for solid-phase peptide synthesis. Common coupling reagents used for the construction of peptide bonds include carbodiimides, N , N -dicyclohexylcarbodiimide (DCC) and N , N -diisopropylcarbodiimide (DIPCDI) for butyloxycarbonyl (Boc) and 9-fluorenylmethyloxycarbonyl (Fmoc) strategies, respectively, active esters such as pentafluorophenyl derivatives (OPfp) and uronium and phosphonium salts based on N -hydroxybenzotriazole (HOBt). Fmoc amino acid fluorides and urethane-protected N-carboxyanhydrides (UNCA's) are also efficient reagents for rapid peptide coupling under both solution and solid-phase conditions. l-hydroxy-7-azabenzotriazole (HOAt), HATU, PyAOP, HAPyU and tetramethyl fluoroformamidinium hexafluorophosphate (TFFH) are efficient coupling reagents for solution- and solid-phase peptide synthesis. These derivatives enhance reactivity, reduce racemization and are suited for peptides containing either natural or hindered amino acids. These reagents are compatible with both manual and automated batch and continuous-flow techniques.

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