Naslov
A practical synthesis of Nalpha-Fmoc protected L-threo-beta-hydroxyaspartic acid derivatives for coupling via alpha- or beta-carboxylic group

Autori
Bionda, Nina ; Čudić, Mare ; Barišić, Lidija ; Stawikowski, Maciej ; Stawikowska, Roma ; Binetti, Diego ; Čudić, Predrag

Izvornik
Amino acids (Wien) (0939-4451) 42 (2012), 1; 285-293

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
hydroxyaspartic acid; enantioresolution; orthogonal protection; Fmoc solid-phase peptide synthesis

Sažetak
A simple and practical general synthetic protocol towards orthogonally protected tHyAsp derivatives fully compatible with Fmoc solid-phase peptide synthetic methodology is reported. Our approach includes enantioresolution of commercially available D, L-tHyAsp racemic mixture by co-crystallization with L-Lys, followed by ion exchange chromatography yielding enantiomerically pure L-tHyAsp and D-tHyAsp, and their selective orthogonal protection. In this way Na-Fmoc protected tHyAsp derivatives were prepared ready for couplings via either a- or b-carboxylic group onto the resins or the growing peptide chain. In addition, coupling of tHyAsp via b-carboxylic group onto amino resins allows preparation of peptides containing tHyAsn sequences, further increasing the synthetic utility of prepared tHyAsp derivatives.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA