期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 14, 页码 3116-3120出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500142
关键词
Peptides; Synthetic methods; Solid-phase synthesis; Peptide coupling; Steric hindrance
资金
- National Research Foundation (NRF) of the University of KwaZulu-Natal (South Africa)
- Secretaria Nacional de Educacion Superior, Ciencia, Tecnologia e Innovacion (SENESCYT), Ecuador
- Centro de Investigacion Cientifica y Tecnologica (CICYT) [CTQ2012-30930]
- Generalitat de Catalunya [2014 SGR 137]
- Institute for Research in Biomedicine, Barcelona (IRB Barcelona, Spain)
- Deanship of Scientific Research at King Saud University (Saudi Arabia) [RGP-234]
Nowadays, DIC is the most widely used carbodiimide for solid-phase peptide synthesis, while EDC center dot HCl is mostly used only for solution-phase synthesis. In this paper, we report new coupling cocktails containing EDC center dot HCl in combination with potassium salts of OxymaPure and Oxyma-B (i.e., K-Oxyma and K-Oxyma-B, respectively). These reagent cocktails gave spectacular purity compared to DIC/classical N-hydroxylamine derivatives in the solid-phase peptide synthesis of the Aib-enkephaline (Aib = 2-aminoisobutyric acid) pentapeptide (H-Tyr-Aib-Aib-Phe-Leu-NH2), a hindered peptide. Furthermore, we found that the EDC center dot HCl/K-Oxyma combination can be used with DMF, THF, or MeCN as the solvent. The optimized cocktail gave less racemization than benzotriazole derivatives, but slightly more than OxymaPure and Oxyma-B during stepwise solution-phase peptide synthesis.
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