Microwave-Assisted Synthesis of 2,2 '-Azopyridine-Labeled Amines, Amino Acids, and Peptides

AVAN İ.

SYNTHESIS-STUTTGART, vol.48, no.3, pp.365-378, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 48 Issue: 3
  • Publication Date: 2016
  • Doi Number: 10.1055/s-0035-1560523
  • Journal Name: SYNTHESIS-STUTTGART
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.365-378
  • Keywords: 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 University Affiliated: Yes

Abstract

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.