ArticleBioorganic & medicinal chemistry letters2008
Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26.
Article in Bioorganic & medicinal chemistry letters, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 26 citations in OpenAlex.
- Direct Asymmetric α-C Conjugate Addition of Aminomethylphosphonate Enabled by Carbonyl/Iminium Double Organoactivation.Nature communications · 2026Article
- From Discovery to Manufacturing: A Quantitative Review of Phosphonates and Strategies for High-Titer Production.Microorganisms · 2026Review
- Article
- Zirconium-catalyzed asymmetric Kabachnik-Fields reactions of aromatic and aliphatic aldehydes.Chemical science · 2021Article
- Discovery of the Tyrobetaine Natural Products and Their Biosynthetic Gene Cluster via Metabologenomics.ACS chemical biology · 2018Article
- Interkingdom pharmacology of Angiotensin-I converting enzyme inhibitor phosphonates produced by actinomycetes.ACS medicinal chemistry letters · 2014Article
- Revisiting the biosynthesis of dehydrophos reveals a tRNA-dependent pathway.Proceedings of the National Academy of Sciences of the United States of America · 2013Article
- Structure-activity relationships of the phosphonate antibiotic dehydrophos.Chemical communications (Cambridge, England) · 2010Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The naturally occurring phosphonotripeptide K-26 is a potent angiotensin converting enzyme (ACE) inhibitor containing an alpha-amino phosphonic acid analogue of tyrosine. Previous studies have demonstrated that canonical peptide analogues of K-26 are micromolar inhibitors of ACE. To ascertain the structure-activity relationships in this class of ACE inhibitory natural products, K-26 and eight analogues were chemically synthesized and evaluated. Phosphonyl substitution was found to be the critical determinant of activity, resulting in a 1500-fold increase in ACE inhibition versus carboxyl analogues. Secondarily, the absolute configuration of the terminal alpha-amino phosphonate and N-acetylation were found to significantly modulate ACE inhibitory activity.
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Registered trials
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