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Cardiolipin Prevents Membrane Translocation and Permeabilization by Daptomycin*
The collective findings lead to propose that a daptomycin pore consists of two aligned tetramers in opposite leaflets and that cardiolipin prevents the translocation of tetramer to the inner leaflet, thereby forestalling the formation of complete, octameric pores. Expand
The action mechanism of daptomycin.
Novel methods of total synthesis, including a recent one that is carried out entirely on a solid phase, will enable a more thorough and systematic exploration of the sequence space of daptomycin. Expand
Synthesis and protection of aryl sulfates using the 2,2,2-trichloroethyl moiety.
The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates and was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies. Expand
Characterization of daptomycin oligomerization with perylene excimer fluorescence: stoichiometric binding of phosphatidylglycerol triggers oligomer formation.
Perylene excimer fluorescence is used to characterize the membrane-associated oligomer of daptomycin and shows that the N-terminal acyl chains of neighboring oligomer subunits are in immediate contact with one another. Expand
Two successive calcium-dependent transitions mediate membrane binding and oligomerization of daptomycin and the related antibiotic A54145.
These findings agree with the earlier observation that two of the four acidic amino acid residues in the daptomycin molecule are essential for antibacterial activity. Expand
The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors.
A comparison of peptide 7 with analagous peptides bearing other monoanionic pTyr mimetics recently reported in the literature indicates that F(2)Smp is about 65-fold more effective than any other non-hydrolyzable, monanionic p tyr mimetic reported to date. Expand
Solid-phase total synthesis of daptomycin and analogs.
An entirely solid-phase synthesis of daptomycin, a cyclic lipodepsipeptide antibiotic currently in clinical use, was achieved using a combination of α-azido and Fmoc amino acids. This methodology wasExpand
Multiple Pathways for the Irreversible Inhibition of Steroid Sulfatase with Quinone Methide‐Generating Suicide Inhibitors
Kinetic studies suggest that inhibition by the monofluoro derivatives is a result of a quinone methide intermediate that reacts with active‐site nucleophiles, whereas the main inhibition pathway of the 4‐difluoromethyl derivative isA result of decomposition of the initial quin one methide to an aldehyde that acts as potent, almost irreversible inhibitor. Expand
Boronic acids as inhibitors of steroid sulfatase.
Results suggest that the boronic acid moiety must be attached to a platform very closely resembling a natural substrate in order for it to impart a beneficial effect on binding affinity compared to its phenolic analog. Expand