4.5 Article

K-Oxyma: a Strong Acylation-Promoting, 2-CTC Resin-Friendly Coupling Additive

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 28, Pages 6372-6378

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300777

Keywords

Solid-phase synthesis; Peptides; Acylation; Acid-labile solid supports

Funding

  1. Secretaria de Estado de Cooperacion Internacional (AECI)
  2. Centro de Investigacion Cientifica y Tecnologica (CICYT) [CTQ2012-30930]
  3. Generalitat de Catalunya [2009SGR 1024]
  4. 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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