Preparative and synthetic laboratory
Facility manager: Viktória Goldschmidt Gőz, PhD
Members: Bence Balterer, Dr. Viktor Farkas, Viktória Goldschmidt Gőz, PhD, Tímea Baló, Adrienn Kiss, Kristóf Ferentzi, Elina Sarolta Lajtos , Dorina Máté, Dr. István Pintér, Szebasztián Szaniszló , István Varga, Gergő Hegedűs, Duong Kim Hoang Yen, Berill Ónodi, Gréta Nagy, Adrienn Nagy
By using modern organic chemistry methods we are synthesising different carbohydrate derivatives, beta amino acid residues, oligo- and polypeptides and chimeras. The total synthesis and the condensation reactions of both hydrophilic and hydrophobic, five- and six-membered ring containing amino acids are completed. Working on these monomers both cost efficiency and the possibility to scale up the synthetic method are among our goals. The optically active building units are used for the synthesis of foldamers.
Approaches to Pyranuronic β-Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers
Pyranuronic β-sugar amino acids (β-SAAs) are biocompatible and tuneable building blocks of foldamers and α/β chimera peptides. The scalable and economical total synthesis of two building blocks was described. These C-4 epimers, Fmoc-GlcAPU(Me)-OH and Fmoc-GalAPU(Me)-OH, which are suitable for solid phase peptide synthesis, were prepared via a common oxime intermediate. The new synthesis uses nine consecutive steps, starting from methyl α-D-glucopyranoside. The synthesis is fine-tuned, optimized, and ready for largescale and cost-efficient production.
Eur. J. Org. Chem. 2018, 355
New building blocks synthesized: just published in Amino Acids
„C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies”. Yield optimized, scalable and environment-friendly protocols for making β-sugar amino acids and their derivatives to built up α/β-chimera peptides.
More news from the lab.
Our recent paper in Amino Acids explains why the application of Ph3P as Staudinger reagent is "ineffective" in the case of sterically hindered azido-compounds during solid phase peptide syntheses.
E.Fischer's 100 years old question answered on arylhydrazone stability
Our paper, Hydrogen-Bonding Network Anchors the Cyclic Form of Sugar Arylhydrazones (DOI: 10.1002/ejoc.201600462), has been accepted in EurJOC. Congratulations Viki!
Adrienn Nagy , Barbara Csordás , Virág Zsoldos-Mády , István Pintér , Viktor Farkas , András Perczel
C‐3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies
Amino Acids 49(2):223–240. | doi: 10.1007/s00726-016-2346-5 | PMID: 27803987 (2017) Kivonat