88739-85-9Relevant academic research and scientific papers
Synthesis, preferred conformation, and membrane activity of medium-length peptaibiotics: Tylopeptin B
Gobbo, Marina,Poloni, Claudia,De Zotti, Marta,Peggion, Cristina,Biondi, Barbara,Ballano, Gema,Formaggio, Fernando,Toniolo, Claudio
experimental part, p. 169 - 181 (2011/02/23)
The solid-phase synthesis and full chemical characterization of the medium-length (14-amino acid residues) peptaibol with antibiotic properties of tylopeptin B, originally extracted from the fruiting body of the mushroom Tylopilus neofelleus, are described. These data are accompanied by the results on the solution-phase synthesis via the segment condensation approach of a selected, side-chain protected, analog. A solution conformational analysis, performed by the combined use of FTIR absorption, circular dichroism, and 2D-NMR (the latter technique coupled to molecular dynamics calculations), favors the conclusion that the 3D-structure of tylopeptin B is largely helical with a preference for the α- or the 310-helix type depending upon the nature of the solvent. Helix topology and (partial) amphiphilic character are responsible for the observed membrane-modifying properties of this peptaibiotic.
PEPTIDIC COMPOUNDS
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Page/Page column 69-70, (2008/06/13)
The present invention provides a compound of formula (I), (II), (III) and (IV) as defined herein and pharmaceutically acceptable derivatives thereof. The present invention further provides use of the compounds of the present invention in the treatment of bacterial infection and in the treatment of HIV infection. Also provided are pharmaceutical compositions comprising the compounds of the present invention.
Synthesis of chiral, nonracemic methyleneaziridines derived from β-amino alcohols
Ince, Julie,Ross, Tracey M.,Shipman, Michael,Ennis, David S.
, p. 3397 - 3406 (2007/10/03)
An efficient three step process for the synthesis of chiral, nonracemic methyleneaziridines derived from homochiral β-amino alcohols is described. Methyleneaziridines 4a-e produced using this chemistry have been shown to possess high enantiomeric purities
Remarkable Effects of Lone Pair-Lone Pair Interactions on the Extremely Stereoselective Cycloaddition of Azidoketene to Chiral 3-Imino-β-lactams
Ojima, Iwao,Nakahashi, Kazuaki,Brandstadter, Stephan M.,Hatanaka, Naoto
, p. 1798 - 1805 (2007/10/02)
The stereoselective cycloaddition of azidoketene to cis-3-imino-β-lactams 1, 2, and 3, trans-3-imino-β-lactam 4, and cis-3-iminoazetidine 5 were carried out.It was found that the reactions of 1, 2, and 3 proceeded with > 99.5 percent stereoselectivity to give bis-β-lactams 9, 14, and 19, respectively.The reaction of 4 gave a bis-β-lactam 20 with 62 percent de, and the reaction of 5 gave a β-lactamazetidine 21 with 32 percent de including the asymmetry in the opposite direction.These results clearly indicate that, in addition to the conventional steric effects, the lone pair-lone pair interaction of β-lactam oxygen with the intermediate betaine's oxygen is the crucial factor for the extremely stereoselective cycloaddition of azidoketene to 1, 2, and 3.Possible mechanisms for these stereoselective cycloadditions are proposed.The X-ray crystal structure of 3a and the calculated energy-minimum conformations of 3a, 4, and 5 with MODEL-MM2-ROTOCHEM programs are provided.
