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Katherine Nott Michel Paquot Samuel Dufour Marc Eeman Magali Deleu 《Colloids and surfaces. B, Biointerfaces》2009,69(2):268-275
Three kinds of derivatives of the M1 factor of virginiamycin have been synthesised: esters with long chain fatty acids, oximes with modified polar amino acids and bis-derivatives with both the ester and oxime function. The study of the surface tension time dependence of M1 and its derivatives has shown that it is necessary to enhance simultaneously the hydrophobicity and the hydrophilicity of M1 to render M1 surface-active. A structure/function relationship study of the surface-active bis-derivatives has shown that enhancing the hydrophobicity of the molecule led to slower adsorption kinetics, higher stability of the monolayers formed and a better capacity to penetrate a membrane model. The repulsive electrostatic forces due to the presence of charges on the amino acids linked to M1 lead to higher surface tensions, a greater molecular area at the interface and lower penetration into a membrane model.This study has demonstrated that modifying systematically the hydrophobicity and hydrophilicity of a non surface-active molecule allows the production of surface-active derivatives. 相似文献
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Katherine Nott Samuel Dufour Sylvie Heilporn Patrick Rollin Georges Lognay Michel Paquot 《Tetrahedron letters》2005,46(43):7377-7380
An efficient chemoselective ligation approach using an oxime bond was developed for the synthesis of amino acid derivatives of virginiamycin M1, a highly sensitive streptogramin antibiotic. 相似文献
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Jennifer L. Robinson 《Tetrahedron letters》2004,45(10):2147-2150
Described are the syntheses of four macrocyclic peptides that are the core structure of class B synergimycins, and the synthesis of a final class B derivative. Our synthetic route to these synergimycin derivatives allows the incorporation of amino acid substitutions at all points in the macrocycle, leading to structurally diverse class B analogs. 相似文献
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K. Nott M. Paquot S. Heilporn F. Gosselé J. Giard P. Gerbaux G. Lognay B. Wathelet 《Chromatographia》2002,56(5-6):331-335
Summary The goal of this study was to develop a simple, fast and reliable procedure for the preparation of highly purified virginiamycin
M1 factor using readily available and low cost laboratory equipment. This was achieved by purifying M1 by reversed-phase flash chromatography after clean-up of the bulk sample by filtration on a silica gel cake. The purity of
the final product determined by RP-HPLC was 99% and its identity was confirmed by IR spectroscopy and ESI mass spectrometry. 相似文献
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Modular, fully synthetic routes to structurally complex natural products provide useful avenues to access chemical diversity. Herein we report a concise route to virginiamycin M2, a member of the group A streptogramin class of natural products that inhibits bacterial protein synthesis. Our approach features a longest linear sequence of six steps from 7 simple building blocks, and is the shortest and highest yielding synthesis of any member of the streptogramin class reported to date. We believe this route will enable access to unexplored structural diversity and may serve as a useful tool to improve the therapeutic potential of the streptogramin class of antibiotics. 相似文献
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