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Synthesis and biological evaluation of purpurealidin E-derived marine sponge metabolites: aplysamine-2, aplyzanzine A, and suberedamines A and B.
Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit and have been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Expand
Effects of proline analog binding on the spectroscopic and redox properties of PutA.
A proline analog is identified that will be useful for testing the role substrate binding has in regulating PutA functions and is found to display simple competitive inhibition of proline dehydrogenase activity in PutA. Expand
Synthesis and kinetic analysis of some phosphonate analogs of cyclophostin as inhibitors of human acetylcholinesterase.
Kinetic analysis indicates both a binding and a slow inactivation step for all active compounds and mass spectrometric analysis indicates that the active site Ser is indeed phosphorylated by the bicyclic phosphonate. Expand
Rat hormone sensitive lipase inhibition by cyclipostins and their analogs.
It is reported here that synthesized individual diastereomers of cyclipostins P and R have nanomolar IC50s toward hormone sensitive lipase (HSL), indicating a critical SAR for these compounds, the hydrophobic tail. Expand
The first total synthesis of (±)-cyclophostin and (±)-cyclipostin P: inhibitors of the serine hydrolases acetyl cholinesterase and hormone sensitive lipase.
The inhibition [IC(50)] of human AChE by cyclophostin and its diastereomer are reported, as well as constituent binding (K(I)) and reactivity (k(2)) constants. Expand
Cyclophostin and Cyclipostins analogues, new promising molecules to treat mycobacterial-related diseases.
The results support the fact that a panel of Cyclophostin and Cyclipostins analogues represent a new family of potent and selective inhibitors against mycobacteria, especially against M. abscessus, the most drug-resistantMycobacterial species. Expand
Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: synthesis of verongamine and purealidin N.
The oxidation of tyrosine ethyl ester (7) with Na(2)WO(4)/H(2)O(2) in ethanol, dimethyldioxirane in acetone, or methyltrioxorhenium/H(2)O(2) in EtOH gave the corresponding tyrosine oxime (8) in highExpand
Efficient synthesis of tyrosine-derived marine sponge metabolites via acylation of amines with a coumarin.
Oxidative spirocyclization of three representative phenolic oximes with polymer-supported (diacetoxyiodo) benzene gave the spiroisoxazolines. Expand
Synthesis and kinetic evaluation of cyclophostin and cyclipostins phosphonate analogs as selective and potent inhibitors of microbial lipases.
The powerful and selective inhibition of microbial (fungal and mycobacterial) lipases suggests that these seven-membered monocyclic enol-phosphonates should provide useful leads for the development of novel and highly selective antimicrobial agents. Expand
Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.
A convergent synthesis of the C(18)-C(34) fragment of amphidinolide C and the C-18-C(29) fragment from the common intermediate tetrahydrofuranyl-β-ketophosphonate is reported. Expand