Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 19, Pages 3641-3649Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000314
Keywords
Solid-phase synthesis; Peptides; Amides; Coupling reagents; Chirality
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Funding
- Centro de Investigacion Cientifica y Tecnologica (CICYT) [CTQ2009-07758]
- Generalitat de Catalunya [2009SGR 1024]
- Institute for Research in Biomedicine
- Barcelona Science Park
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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.
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