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K‐Oxyma: a Strong Acylation‐Promoting, 2‐CTC Resin‐Friendly Coupling Additive
Author(s) -
Cherkupally Prabhakar,
Acosta Gerardo A.,
NietoRodriguez Lidia,
Spengler Jan,
Rodriguez Hortensia,
Khattab Sherine N.,
ElFaham Ayman,
Shamis Marina,
Luxembourg Yoav,
Prohens Rafel,
SubirosFunosas Ramon,
Albericio Fernando
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300777
Subject(s) - chemistry , epimer , acylation , solubility , hydroxylamine , peptide bond , salt (chemistry) , combinatorial chemistry , decomposition , organic chemistry , environmentally friendly , potassium , medicinal chemistry , stereochemistry , ecology , biology , enzyme , catalysis
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.