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Synthesis 2016; 48(03): 365-378
DOI: 10.1055/s-0035-1560523
DOI: 10.1055/s-0035-1560523
paper
Microwave-Assisted Synthesis of 2,2′-Azopyridine-Labeled Amines, Amino Acids, and Peptides
Further Information
Publication History
Received: 21 July 2015
Accepted after revision: 16 October 2015
Publication Date:
27 October 2015 (online)
Dedicated to the memory of Alan Roy Katritzky (1928–2014)
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.
Key words
azopyridine - microwave synthesis - N-acylbenzotriazole - acylation - peptides - photoisomerization - cis–trans isomerizationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560523.
- Supporting Information
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