Novel highly emissive non-proteinogenic amino acids: synthesis of 1,3,4-thiadiazolyl asparagines and evaluation as fluorimetric chemosensors for biologically relevant transition metal cations

• Published in: Amino acids Vol. 40; no. 4; pp. 1065 - 1075
• Main Authors: Esteves, Cátia I. C, Raposo, M. Manuela M, Costa, Susana P. G
• Format: Journal Article
• Language: English
• Published: Vienna Vienna : Springer Vienna 01.04.2011; Springer Vienna; Springer Nature B.V
• Subjects: Amino acids; Analytical Chemistry; asparagine; Asparagine - analogs & derivatives; Asparagine - metabolism; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; Biosensing Techniques - methods; Cations; Cations - analysis; Cations - metabolism; Chains; Chemosensors; Chromatography, Gel; Constants; Derivatives; Electrons; Emissivity; Fluorescence; Kinetics; Life Sciences; Limit of Detection; Mathematical analysis; Neurobiology; Non-proteinogenic amino acids; Original Article; Proteomics; Spectrometry, Fluorescence; Thiadiazole; Thiadiazoles - chemical synthesis; Thiadiazoles - metabolism; Transition Elements - analysis; Transition Elements - metabolism; Transition metals; Asparagine; Fluorescence; Transition metals; Non-proteinogenic amino acids; Thiadiazole; Chemosensors
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-010-0730-0

Highly emissive heterocyclic asparagine derivatives bearing a 1,3,4-thiadiazolyl unit at the side chain, functionalised with electron donor or acceptor groups, were synthesised and evaluated as amino acid-based fluorimetric chemosensors for metal cations, such as Cu²⁺, Zn²⁺, Co²⁺ and Ni²⁺. The results suggest that there is a strong interaction through the donor heteroatoms at the side chain of the various asparagine derivatives, with high sensitivity towards Cu²⁺ in a ligand-metal complex with 1:2 stoichiometry. Association constants and detection limits for Cu²⁺ were calculated. The photophysical and metal ion sensing properties of these asparagine derivatives confirm their potential as fluorimetric chemosensors and suggest that they can be suitable for incorporation into chemosensory peptidic frameworks.