AI Article Synopsis
- The total synthesis of Microcin SF608 is detailed, showcasing the complexity of creating this compound.
- Access to its crucial octahydroindole core structure comes from a specific chemical reaction involving TMSOTf and NEt(3) to open an oxabicyclic ring.
- Key techniques used include a precise epoxide reduction and the use of photolytic excision to remove a tertiary alcohol.
Article Abstract
The total synthesis of Microcin SF608 is reported. Access to the octahydroindole core structure of Microcin SF608 relies on the TMSOTf/NEt(3)-mediated opening of an oxabicyclic ring system. Additional highlights of the synthetic strategy that is reported include a highly regioselective epoxide reduction and photolytic excision of a 3 degrees alcohol.
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Access to the aeruginosin serine protease inhibitors through the nucleophilic opening of an oxabicyclo[2.2.1]heptane: total synthesis of microcin SF608.
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Serine proteases play key roles in many biological processes and are associated with several human diseases such as thrombosis or cancer. During the search for selective inhibitors of serine proteases, a family of linear peptides named the aeruginosins was discovered in marine cyanobacteria. We herein report an entry route into the synthetically challenging core fragment of these natural products.
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Raymond and Beverly Sackler School of Chemistry and Faculty of Exact Sciences, Tel-Aviv University, Ramat Aviv, Tel-Aviv 69978, Israel.
Nine new metabolites, aeruginosins DA495A (1), DA511 (2), DA642A (3), DA642B (4), DA688 (5), DA722 (6), and DA495B (7), microguanidine DA368 (8), and anabaenopeptin DA850 (9), were isolated along with the known micropeptins MZ924, MZ939A, and MZ1019, cyanopeptolins S and SS, microcin SF608, and aeruginazoles DA1497, DA1304, and DA1274 from bloom material of the cyanobacterium Microcystis aeruginosa collected from the Dalton reservoir, Israel, in October 2007. Their structures were elucidated by a combination of various spectroscopic techniques, primarily NMR and MS, while the absolute configurations of the asymmetric centers were determined by Marfey's and chiral-phase HPLC methods. Two of the new aeruginosins, DA511 (1) and DA495A (2), contain a new Choi isomer, (2S,3aS,6S,7aS)-Choi.
View Article and Find Full Text PDFSynthesis of Microcin SF608 through nucleophilic opening of an oxabicyclo[2.2.1]heptane.
Org Lett
September 2010
Laboratorium für Organische Chemie, ETH-Hönggerberg, HCI, H335, CH-8093 Zürich, Switzerland.
Article Synopsis
- The total synthesis of Microcin SF608 is detailed, showcasing the complexity of creating this compound.
- Access to its crucial octahydroindole core structure comes from a specific chemical reaction involving TMSOTf and NEt(3) to open an oxabicyclic ring.
- Key techniques used include a precise epoxide reduction and the use of photolytic excision to remove a tertiary alcohol.
Effects of microcin SF608 and microcystin-LR, two cyanotobacterial compounds produced by Microcystis sp., on aquatic organisms.
Environ Toxicol
October 2002
Institute of Biology (Genetics), Humboldt University, Chausseestrasse 117, 10115 Berlin, Germany.
Effects of two cyanobacterial compounds, microcin SF608 and microcystin-LR, were investigated on different physiological parameters of two organisms, the water moss, Vesicularia dubyana, and the waterflea, Daphnia magna. Both compounds are produced by Microcystis species. Microcystin-LR is a potent inhibitor of protein phosphatases 1 and 2A, and microcin SF608 inhibits serine proteases.
View Article and Find Full Text PDFSynthesis of microcin SF608.
J Org Chem
July 2002
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.
The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.
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