Parallel synthesis of peptide-like macrocycles containing imidazole-4,5-dicarboxylic acid.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Zhigang XuPaul W Baures

Abstract

We prepared a series of peptide-like 14-membered macrocycles containing an imidazole-4,5-dicarboxylic acid scaffold by using known coupling reagents and protecting group strategies. Yields of the purified macrocycles were poor on average, yet seemingly independent of amino acid substitution or stereochemistry. The macrocycles retain some level of conformational variability as observed by both molecular modeling and X-ray crystallography. These macrocycles represent a new class of structures for further development and for future application in high-throughput screening against a variety of biological targets.

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Citations

Jun 4, 2019·Chemical Reviews·Ivan V SmolyarValentine G Nenajdenko

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Methods Mentioned

BETA
column chromatography
X-ray

Software Mentioned

XPREP
93
Spartan
SHELXL
SAINT

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