PotM: Smoc Amino Acids

For the production of synthetic peptides, every year tens of thousands of tons of organic solvents are required in the chemical, cosmetic and pharmaceutical industries. According to the European Chemicals Directive REACH, these solvents are classified as substances of very high concern and their use is associated with significant risks for health and the environment. Following modern regulatory rules, “undesirable” solvents such as DCM, DMF, NMP and THF, which are frequently recommended and employed during SPPS, should be replaced.

At the same time, the enormous consumption of solvents and reagents leads to high production costs.

Thus, despite being considered as advanced and efficient technique for peptide production, solid-phase peptide synthesis (SPPS) is associated with severe drawbacks. Therefore, ongoing attempts aim at developing alternative approaches using solvents, which are permitting to reduce the risks for environment and human health.

Thanks to the Clean Peptide Technology (CPT), manufacturing of peptides can be eco-friendly and take place at significantly lower costs: the application of water-compatible 2,7-disulfo-9-fluorenylmethoxycarbonyl (Smoc) amino acids makes industrial peptide production possible without having to use organic solvents. Amino acids bearing the Smoc group at the N-terminus possess both high water solubility and pronounced fluorescence, which allow for real-time monitoring. As a solid support, a water-swellable resin can be used.

Schematic illustration of the Peptide Clean Technology.

Cleavage of the Smoc group can be achieved using aqueous piperidine, piperazine, sodium hydroxide, ethanolamine, and ammonia to liberate the N-terminus within 5-15 minutes at ambient temperature together with the formation of the respective disulfonated dibenzofulvene and the products of water or base addition.

Moreover, there is also a concept for a simple waste water treatment, an efficient product purification (can be used as pre-purification) and a real-time monitoring of the reaction progress, leading to total production cost savings of up to 50%.

Be part of the change! Companies that use the CPT can clearly position themselves for a sustainable and more environmentally friendly peptide production form.

➔ Discover Smoc amino acids available at Iris Biotech – see the related products at the bottom of this page!

➔ Need more information? Register for our workshop on the Clean Peptide Technology!

References:

Sustainable Peptide Synthesis Enabled by a Transient Protecting Group; S. Knauer, N. Koch, C. Uth, R. Meusinger, O. Avrutina, H. Kolmar; Angew. Chem. Int. Ed. Engl. 2020; 59(31): 12984-12990. https://doi.org/10.1002/anie.202003676

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