ArticleJournal of the American Chemical Society2014
Synthesis of a des-B-ring bryostatin analogue leads to an unexpected ring expansion of the bryolactone core.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 31 citations in OpenAlex.
- Function-Oriented Synthesis: Design, Synthesis, and Evaluation of Highly Simplified Bryostatin Analogues.The Journal of organic chemistry · 2020Article
- Deletion of the C26 Methyl Substituent from the Bryostatin Analogue Merle 23 Has Negligible Impact on Its Biological Profile and Potency.Chembiochem : a European journal of chemical biology · 2018Article
- A Synthesis of Exiguaquinol Dessulfate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Replacement of the Bryostatin A- and B-Pyran Rings With Phenyl Rings Leads to Loss of High Affinity Binding With PKC.Tetrahedron letters · 2016Article
- Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C-C Bond Formation: Potency Does Not Confer Bryostatin-like Biology.Journal of the American Chemical Society · 2016Article
- Simplified Bryostatin Analogues Protect Cells from Chikungunya Virus-Induced Cell Death.Journal of natural products · 2016Article
- Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.Angewandte Chemie (International ed. in English) · 2016Review
- Conformation-activity relationships of polyketide natural products.Natural product reports · 2015Review
- Neristatin 1 provides critical insight into bryostatin 1 structure-function relationships.Journal of natural products · 2015Article
- Toward a biorelevant structure of protein kinase C bound modulators: design, synthesis, and evaluation of labeled bryostatin analogues for analysis with rotational echo double resonance NMR spectroscopy.Journal of the American Chemical Society · 2015Article
- Synthesis of seco-B-ring bryostatin analogue WN-1 via C-C bond-forming hydrogenation: critical contribution of the B-ring in determining bryostatin-like and phorbol 12-myristate 13-acetate-like properties.Journal of the American Chemical Society · 2014Article
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Authors and funding
7 authors at 4 institutions in 1 country.
Funding
Abstract
A convergent synthesis of a des-B-ring bryostatin analogue is described. This analogue was found to undergo an unexpected ring expansion of the bryolactone core to generate the corresponding 21-membered macrocycle. The parent analogue and the ring-expanded product both displayed nanomolar binding affinity for PKC. Despite containing A-ring substitution identical to that of bryostatin 1 and displaying bryostatin-like biological function, the des-B-ring analogues displayed a phorbol-like biological function in cells. These studies shed new light on the role of the bryostatin B-ring in conferring bryo-like biological function to bryostatin analogues.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.