Microwave-Assisted Synthesis of 2,2 '-Azopyridine-Labeled Amines, Amino Acids, and Peptides
SYNTHESIS-STUTTGART, cilt.48, sa.3, ss.365-378, 2016 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 48 Sayı: 3
- Basım Tarihi: 2016
- Doi Numarası: 10.1055/s-0035-1560523
- Dergi Adı: SYNTHESIS-STUTTGART
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
- Sayfa Sayıları: ss.365-378
- Anahtar Kelimeler: azopyridine, microwave synthesis, N-acylbenzotriazole, acylation, peptides, photoisomerization, cis-trans isomerization, PHOTORESPONSIVE CROWN-ETHERS, DNA-BINDING SPECIFICITY, THERAPEUTIC PEPTIDES, PHOTOCHEMICAL REGULATION, AZOBENZENE, PHOTOCONTROL, LIGHT, PROTEIN, PROBE, PHOTOREGULATION
- Anadolu Üniversitesi Adresli: Evet
Özet
A microwave-assisted procedure for labeling amines, amino acids, and peptides with 2,2'-azopyridines (2,2'-AzPy) is described using the corresponding 2,2'-azopyridine-diacylbenzotriazoles. The efficiency of the procedure is proven by the generation of three constitutionally isomeric sets of 2,2'-AzPy-X,X'-labeled amino conjugates (where X = 4, 5, 6) including amines, amino acids, and peptides. Microwave- assisted synthesis conditions provide good to excellent yields in less than 15 minutes with retention of original chirality. A trans-to-cis isomerization of the 2,2'-azopyridine-labeled amino conjugate upon laser irradiation at 325 nm is visualized with UV and NMR spectroscopy.