1240264-13-4Relevant academic research and scientific papers
A novel family of onium salts based upon isonitroso meldrum's acid proves useful as peptide coupling reagents
El-Faham, Ayman,Subiros-Funosas, Ramon,Albericio, Fernando
experimental part, p. 3641 - 3649 (2010/09/03)
A new family of uronium salts (HTMU, HMMU, and HDmPyMU) based on isonitroso Meldrum's acid (HONM) are reported as stand-alone coupling reagents. Amide bond formation with the use of these reagents occurred more quickly than that with other uronium salts as a result of the presence of a neighboring group effect with a cyclic structure. Thus, these novel onium salts were often more effective in the acylation of poor nucleophiles and in the control of optical purity than related Oxyma- and benzotriazole-based reagents. Among the HONM derivatives, HMMU showed the best performance in reducing racemization and assembling demanding sequences such as the Aib-ACP decapeptide or analogues of Leu-enkephalin pentapeptide, Furthermore, the scope and limitations of the use of HONM as an additive in combination with carbodiimides is discussed.
