Elevating 1-tert-Butyl-3-ethylcarbodiimide
(TBEC) as a Reagent for Sustainable Peptide Synthesis: Quality Assessment
and Minimizing Racemization, Precipitation, and Radical-Induced Side
Reactions by TBEC/Oxyma Couplings in an Environmentally Sensible Solvent
Posted on 2023-06-23 - 14:12
The finding that the widely used peptide coupling reagents
DIC
and Oxyma form the toxic H-CN (McFarland, A. D. Org. Process Res. Dev. 2019, 23, 2099) has prompted studies aimed at H-CN minimization, attained, for
example, by solvent engineering (Erny, M. Org. Process Res. Dev. 2020, 24, 1341) and by substituting DIC with TBEC (Manne, S. R. Org. Process Res. Dev. 2022, 26, 2894). Here, an integrated study of TBEC/Oxyma as peptide couplers is
reported, focusing not only on the performance of TBEC in the couplings
but also on its cost, hazards associated with its use, sustainability
of the route of synthesis, the end of life strategies, as well as
the potential impact of impurities in the reagent on the synthesis.
TBEC/Oxyma-mediated peptide couplings in NBP/EtOAc (1:4) proceeded
with minimal racemization, free of precipitation, and radical side
reactions irrespective of TBEC quality. These results hold great promise
for broad adoption of TBEC/Oxyma in suitable green media as a coupling
strategy for sustainable peptide synthesis from an R&D lab to
a manufacturing plant.
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Pawlas, Jan; Choi, Ji-Hyung; von Bargen, Christoph; Maibom-Thomsen, Sheila; Rasmussen, Jon H.; Ludemann-Hombourger, Olivier (2023). Elevating 1-tert-Butyl-3-ethylcarbodiimide
(TBEC) as a Reagent for Sustainable Peptide Synthesis: Quality Assessment
and Minimizing Racemization, Precipitation, and Radical-Induced Side
Reactions by TBEC/Oxyma Couplings in an Environmentally Sensible Solvent. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.3c00120