ReGreen SPPS: enabling circular chemistry in environmentally sensible solid-phase peptide synthesis
Aiming at greener, scalable methods for cost-efficient peptide synthesis a solid-phase peptide synthesis (SPPS) protocol adhering to the principles of circular chemistry[…]
Aiming at greener, scalable methods for cost-efficient peptide synthesis a solid-phase peptide synthesis (SPPS) protocol adhering to the principles of circular chemistry was developed. The method we term ReGreen SPPS utilizes industrially viable polystyrene/divinylbenzene (PS/DVB) resins as polymer supports, inexpensive ethyl acetate (EtOAc) and dimethylsulfoxide (DMSO) as solvents, is synthetically efficient in terms of equivs of amino acids (AAs) in couplings and amounts of base in Fmoc removals and afforded a model difficult 10-mer peptide in 84% yield and 76% purity. A facile process for reagent and solvent recycling of the waste stream from a SPPS process using greener solvents was developed by a simple protocol for the recovery of EtOAc and DMSO (solvents) as well as the coupling agent ethyl (hydroxyimino)cyanoacetate (Oxyma).
J. Pawlas and J. H. Rasmussen, Green Chem., 2019, 21, 5990.
DOI: 10.1039/c9gc02775k