The first synthesis of the anti-TB cyclic peptide callyaerin A containing a rare (Z)-2,3-diaminoacrylamide bridging motif is reported. Fmoc-formylglycine-diethylacetal was used as a masked equivalent of formylglycine in the synthesis of the linear precursor of callyaerin A. Intramolecular cyclization between the formylglycine residue and the N-terminal amine in the linear peptide precursor afforded the macrocyclic natural product callyaerin A. Synthetic callyaerin A possessed potent anti-TB activity (MIC100 = 32 µM) while its all-amide congener was inactive. Variable temperature NMR studies of both the natural product and its all amide analogue revealed the extraordinary rigidity imposed by this diaminoacrylamide unit on peptide conformation. The work reported herein pinpoints the intrinsic role that the rare (Z)-2,3-diaminoacrylamide moiety confers on peptide bioactivity.
This research output has an Altmetric Attention Score of 16. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 10 March 2018.
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Altmetric has tracked 34,411,289 research outputs across all sources so far. Compared to these this one has done particularly well and is in the 91st percentile: it's in the top 10% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 61,754 research outputs from this source. They typically receive more attention than average, with a mean Attention Score of 7.7. This one has done particularly well, scoring higher than 90% of its peers.
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