Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 28, Pages 6372-6378Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300777
Keywords
Solid-phase synthesis; Peptides; Acylation; Acid-labile solid supports
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Funding
- Secretaria de Estado de Cooperacion Internacional (AECI)
- Centro de Investigacion Cientifica y Tecnologica (CICYT) [CTQ2012-30930]
- Generalitat de Catalunya [2009SGR 1024]
- Institute for Research in Biomedicine Barcelona (IRB Barcelona)
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Here we present a new formulation of the recently introduced OxymaPure additive for peptide bond formation, in which the N-hydroxylamine group is replaced by a potassium salt. The complete suppression of its acidity converts K-Oxyma into the most suitable coupling choice when peptides are assembled on highly acid-labile solid-supports. The coupling efficiency and diminished prospects for epimerization are conserved relative to OxymaPure. In addition, K-Oxyma displays excellent solubility in a variety of organic solvents and undergoes safer decomposition than classical 1-hydroxybenzotriazole additives.
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