Poster Presentation The 16th Australian Peptide Conference 2025

Building with precision - innovative tools in peptide synthesis (#214)

Karin Rustler 1
  1. Iris Biotech GmbH, Marktredwitz, BAYERN, Germany

Iris Biotech offers a broad range of building blocks and reagents specializing in peptide chemistry, with applications spanning life sciences, drug delivery, and linker technologies. True to our slogan „Empowering Peptide Innovation“, we deliver cutting-edge technologies and innovative products tailored for diverse needs—from small-scale research to bulk production—serving academia and industry.

Our recent innovations include novel protecting groups designed to enhance peptide synthesis. The tetrahydropyranyl (THP) group protects serine, threonine, cysteine, and hydroxyproline, while the photosensitve 4-methoxy-7-nitroindolin-1-yl (MNI) group shields aspartate and glutamate [2,3]. These orthogonal protecting groups are compatible with Fmoc-SPPS, offering superior stability and enabling versatile residue modifications.

In the realm of peptide conjugation and cross-linking, we introduce 2-furyl-L-alanine for oxidation-induced furan cross-linking and Diels-Alder reactions, as well as 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one (5HP2O) building blocks [4, 5]. This alternative to maleimides overcomes limitations such as hydrolysis and thiol exchange, offering greater stability and versatility. In this regard, we also introduced next generation maleimides [6, 7].

Our novel amino-Li resin, a cross-linked polyacrylamide-based solid support, is compatible with both organic and aqueous solvents, providing a robust platform for peptide synthesis [8]. Additionally, we present MYTsA , a ynamide coupling reagent that supports both conventional and inverse peptide synthesis (N to C) [9]. MYTsA enhances atom economy and eliminates racemization, setting a new standard in peptide coupling.

[1] Ramos-Tomillero I., Rodriguez H., Albericio F.; Org. Lett. 2015, 17, 7: 1680–1683.

[2] Ramkisson S.,  Al-Rasheed H. H., Dahlous K. A., De La Torre B. G., El-Faham A.,  Albericio F.; ChemistrySelect 2021, 6: 6626-6630.

[3] Tang S., Cheng J.-Y., Zheng J.-S.; Tetrahedron Lett. 2015, 56: 4582-4585.

[4]  Miret-Casals L., Van De Putte S., Aerssens D., Diharce J., Bonnet P., Madder A.; Front. Chem. 2022; 9: 799706.

[5]  De Geyter E., Antonatou E., Kalaitzakis D., Smolen S., Iyer A., Tack L., Ongenae E., Vassilikogiannakis G., Madder A.; Chem. Sci. 2021, 12: 5246-5252.

[6] Nunes J. P. M., Vassileva V., Robinson E., Morais M., Smith M. E. B., Pedley R. B.,  Caddick S., Baker J. R., Chudasama V.; RSC Adv. 2017; 7(40): 24828-24832. 

[7] Wall A., Nicholls K., Caspersen M. B., Skrivergaard S., Howard K. A., Karu K., Chudasama V., Baker J. R.; Org. Biomol. Chem. 2017; 17(34): 7870-7873.

[8] Uth C., Englert S., Avrutina O., Kolmar H., Knauer S.; J Pept. Sci. 2023; 29: e3527.

[9] Liu T., Peng z. , Lai M., Hu L., Zhao J.; J. Am. Chem. Soc. 2024; 146: 4270-4280.