164861-48-7Relevant articles and documents
Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives
Jad, Yahya E.,Acosta, Gerardo A.,Khattab, Sherine N.,De La Torre, Beatriz G.,Govender, Thavendran,Kruger, Hendrik G.,El-Faham, Ayman,Albericio, Fernando
, p. 2393 - 2398 (2015)
To date, DMF has been considered as the only solvent suitable for peptide synthesis. Here we demonstrate the capacity of THF and ACN, which are friendlier solvents than DMF, to yield the product in higher purity than DMF. Using various peptide models, both THF and ACN reduced racemization in solution-phase and solid-phase synthesis when compared with DMF. Moreover, the use of ACN and THF in the solid-phase peptide synthesis of hindered peptides, such as Aib-enkephalin pentapeptide and Aib-ACP decapeptide, in combination with a complete polyethylene glycol resin (ChemMatrix), gave a better coupling efficiency than DMF. This journal is
TOMBU and COMBU as novel uronium-type peptide coupling reagents derived from oxyma-b
Jad, Yahya E.,Khattab, Sherine N.,De La Torre, Beatriz G.,Govender, Thavendran,Kruger, Hendrik G.,El-Faham, Ayman,Albericio, Fernando
, p. 18953 - 18965 (2014)
Here we describe two novel uronium salts, TOMBU and COMBU, derived from the recently described Oxyma-B for use in peptide bond synthesis. These coupling reagents are more stable than COMU in DMF. Furthermore, using various peptide synthetic models in solu
Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents
Klose,El-Faham,Henklein,Carpino,Bienert
, p. 2045 - 2048 (1999)
In the course of comparing the effectiveness of several HOAt- and HOPfp- derived coupling reagents by cyclization and segment condensation of model sequences, using HPLC to follow the time course and to determine the outcome in terms of oligomerization an
EDC·HCl and potassium salts of oxyma and oxyma-b as superior coupling cocktails for peptide synthesis
Jad, Yahya E.,Khattab, Sherine N.,De La Torre, Beatriz G.,Govender, Thavendran,Kruger, Hendrik G.,El-Faham, Ayman,Albericio, Fernando
, p. 3116 - 3120 (2015)
Nowadays, DIC is the most widely used carbodiimide for solid-phase peptide synthesis, while EDC·HCl is mostly used only for solution-phase synthesis. In this paper, we report new coupling cocktails containing EDC·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·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. We have shown that combinations of rather simple and green reagents, such as EDC·HCl and the potassium salt of OxymaPure or Oxyma-B, give unique results in terms of yield and low levels of racemization. We envisage a broad application of these reagents in solid-phase and solution synthesis, and especially in the preparation of peptide-based nanomaterials.
