Synthesis of Purine Nucleoside-Amino Acid Conjugates and Their Photophysical Properties

Tetrahedron 2016
Dace Cīrule, Kristers Ozols, oskars Platnieks, Ilze Māliņa, Ērika Bizdēna, Māris Turks

2,6-Bis-(1,2,3-triazol-1-H-1-yl)purine nucleosides react at C(6) with the N- and S-termini of various amino acids by expelling the corresponding 1,2,3-triazole as a leaving group in nucleophilic aromatic substitution reaction. This gives rise to a novel type of conjugate between purine nucleosides and amino acids. The obtained amino acid-derived 6-amino-2-(1,2,3-triazol-1-H-1-yl)-purine derivatives showed useful levels of fluorescence with quantum yields up to 38% and Stokes shifts up to 91 nm. Glutathione and a cysteine-containing nonapeptide selectively reacted with their S-termini and produced the expected C(6) conjugates in good to excellent yields.

Atslēgas vārdi
Amino acids; Fluorescence; Purine nucleosides; SNAr reactions; Triazolyl purine derivatives
DOI
10.1016/j.tet.2016.05.043
Hipersaite
http://www.sciencedirect.com/science/article/pii/S0040402016304422

Cīrule, D., Ozols, K., Platnieks, O., Māliņa, I., Bizdēna, Ē., Turks, M. Synthesis of Purine Nucleoside-Amino Acid Conjugates and Their Photophysical Properties. Tetrahedron, 2016, Vol.72, Iss.29, 4177.-4185.lpp. ISSN 0040-4020. Pieejams: doi:10.1016/j.tet.2016.05.043

Publikācijas valoda
English (en)