{"id":80107,"date":"2018-03-09T23:26:02","date_gmt":"2018-03-09T23:26:02","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/epoxiamidas-quirales-en-la-sa%c2%adntesis-de-compuestos-bioactivos-sa%c2%adntesis-de-epoxipeptidos-y-de-bengamidas\/"},"modified":"2018-03-09T23:26:02","modified_gmt":"2018-03-09T23:26:02","slug":"epoxiamidas-quirales-en-la-sa%c2%adntesis-de-compuestos-bioactivos-sa%c2%adntesis-de-epoxipeptidos-y-de-bengamidas","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica-de-los-hidratos-de-carbono\/epoxiamidas-quirales-en-la-sa%c2%adntesis-de-compuestos-bioactivos-sa%c2%adntesis-de-epoxipeptidos-y-de-bengamidas\/","title":{"rendered":"Epoxiamidas quirales en la s\u00edntesis de compuestos bioactivos. s\u00edntesis de epoxip\u00e9ptidos y de bengamidas"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Antonio S\u00e1nchez Ru\u00edz <\/strong><\/h2>\n<p>El trabajo descrito en esta tesis es la aplicaci\u00f3n concreta de epoxiamidas quirales obtenidas mediante la condensaci\u00f3n de iluros de azufre estabilizados por una funci\u00f3n amida con aldehidos quirales derivados de carbohidratos. Esta metodolog\u00eda se ha aplicado a la s\u00edntesis de los epoxip\u00e9ptidos e-64, e64c y ca-074, as\u00ed como de amidas an\u00e1logas, y de bengamidas, compuestos bioactivos con un modo de acci\u00f3n a\u00fan por esclarecer. En ambos casos, se ha empleado un iluro de azufre estabilizado por una amida de indolina como compuesto clave, ya que una vez realizada la condensaci\u00f3n, es factible oxidar la epoxiamida de indolina a la indol-amida correspondiente, la cual puede hidrolizarse \u00f3 transamidarse con suavidad. As\u00ed, en el caso de los epoxip\u00e9ptidos, la condensaci\u00f3n de dicho iluro de azufre con el 2,3-o-isopropilid\u00e9n-d-gliceraldeh\u00eddo rindi\u00f3 la expoxiamida de indolina quiral correspondiente en un excelente exceso diasterem\u00e9rico a favor del is\u00f3mero 2s, 3r. Esta exposiamida permite llegar a obtener los compuestos derivados de la familia del e-64c mediante elaboraci\u00f3n del extremo de acetal y acoplamiento con el derivado pept\u00eddico correspondiente, para, posteriormente, oxidar la indolina presenta a u sindol derivado mediante oxidantes radicalarios como el ddq, para, a continuaci\u00f3n, proceder a su hidr\u00f3lisis suave para liberar el \u00e1cido final. no obstante, en el caso de la preparaci\u00f3n del e-64, se hall\u00f3 que la presencia de un grupo bis-boc-guanidino originaba la descomposici\u00f3n de la mol\u00e9cula en la etapa de oxidaci\u00f3n con ddq, siendo necesario partir desde la indolamida derivada del isopropilid\u00e9n-d-gliceraldeh\u00eddo, pudi\u00e9ndose llegar al producto final y a varias amidas an\u00e1logas. Una vez concluida la aproximaci\u00f3n a los exposip\u00e9ptidos, se comenz\u00f3 con la preparaci\u00f3n de las bengamidas, empleando la olefinaci\u00f3n de julia modificada para preparar el alqueno terminal a partir del aldeh\u00eddo derivado del 2,3-o-isopropilid\u00e9n-d-treitol monoprotegido por un si<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Epoxiamidas quirales en la s\u00edntesis de compuestos bioactivos. s\u00edntesis de epoxip\u00e9ptidos y de bengamidas<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Epoxiamidas quirales en la s\u00edntesis de compuestos bioactivos. s\u00edntesis de epoxip\u00e9ptidos y de bengamidas <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Antonio S\u00e1nchez Ru\u00edz <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 M\u00e1laga<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 26\/05\/2006<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li>Francisco Ram\u00f3n Sarabia Garc\u00eda<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: rodrigo Rico  g\u00f3mez <\/li>\n<li>antoni Riera escale (vocal)<\/li>\n<li>Jos\u00e9 Manuel Concell\u00f3n gracia (vocal)<\/li>\n<li> Carda us\u00f3 pedro Miguel (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Antonio S\u00e1nchez Ru\u00edz El trabajo descrito en esta tesis es la aplicaci\u00f3n concreta de epoxiamidas quirales obtenidas [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center 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