{"id":3942,"date":"2017-01-20T15:39:00","date_gmt":"2017-01-20T15:39:00","guid":{"rendered":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/?p=3942"},"modified":"2026-01-26T16:28:05","modified_gmt":"2026-01-26T16:28:05","slug":"thioamide-substitution-to-probe-the-hydroxyproline-recognition-of-vhl-ligands","status":"publish","type":"post","link":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/2017\/01\/20\/thioamide-substitution-to-probe-the-hydroxyproline-recognition-of-vhl-ligands\/","title":{"rendered":"Thioamide substitution to probe the hydroxyproline recognition of VHL ligands"},"content":{"rendered":"<p>The article is a contribution to the journal\u2019s Special Issue for the 2018 Tetrahedron Young Investigators Award for Matthew Fuchter.<\/p>\n<p><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0968089618303481\">Read our article Open Access<\/a><\/p>\n<p>Congratulations Pedro and Xavi, well done!<\/p>\n<div id='gallery-1' class='gallery galleryid-3942 gallery-columns-3 gallery-size-large'><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"464\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-1024x464.jpg\" class=\"attachment-large size-large\" alt=\"Graphical abstract\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-1024x464.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-300x136.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-768x348.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc.jpg 1173w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide.png'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"437\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-1024x437.png\" class=\"attachment-large size-large\" alt=\"n\u2192\u03c0* interaction in prolines and VHL inhibitors\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-1024x437.png 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-300x128.png 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-768x327.png 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-1536x655.png 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide.png 1827w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"444\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-1024x444.jpg\" class=\"attachment-large size-large\" alt=\"Fig. 2. Chemical structure of inhibitor 1 and thioamide derivatives 2\u20134\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-1024x444.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-300x130.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-768x333.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2.jpg 1033w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"442\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-1024x442.jpg\" class=\"attachment-large size-large\" alt=\"Scheme 1. Synthesis of thioamide compounds 2\u20134\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-1024x442.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-300x130.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-768x332.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-1536x663.jpg 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-2048x884.jpg 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"263\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-1024x263.jpg\" class=\"attachment-large size-large\" alt=\"Fig. 3. Biophysical characterization of compounds 1\u20134 binding to VHL.\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-1024x263.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-300x77.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-768x197.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-1536x395.jpg 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-2048x526.jpg 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"511\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-1024x511.jpg\" class=\"attachment-large size-large\" alt=\"Fig. 4. Co-crystal structures of compounds 1\u20134 in complex with VBC.\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-1024x511.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-300x150.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-768x384.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-1536x767.jpg 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-2048x1023.jpg 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure>\n\t\t<\/div>\n\n<p>The article is a contribution to the journal\u2019s Special Issue for the 2018 Tetrahedron Young Investigators Award for Matthew Fuchter.<\/p>\n<p><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0968089618303481\">Read our article Open Access<\/a><\/p>\n<p>Congratulations Pedro and Xavi, well done!<\/p>\n<div id='gallery-2' class='gallery galleryid-3942 gallery-columns-3 gallery-size-large'><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"464\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-1024x464.jpg\" class=\"attachment-large size-large\" alt=\"Graphical abstract\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-1024x464.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-300x136.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc-768x348.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/toc.jpg 1173w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide.png'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"437\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-1024x437.png\" class=\"attachment-large size-large\" alt=\"n\u2192\u03c0* interaction in prolines and VHL inhibitors\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-1024x437.png 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-300x128.png 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-768x327.png 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide-1536x655.png 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/thioamide.png 1827w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"444\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-1024x444.jpg\" class=\"attachment-large size-large\" alt=\"Fig. 2. Chemical structure of inhibitor 1 and thioamide derivatives 2\u20134\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-1024x444.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-300x130.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2-768x333.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f2.jpg 1033w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"442\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-1024x442.jpg\" class=\"attachment-large size-large\" alt=\"Scheme 1. Synthesis of thioamide compounds 2\u20134\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-1024x442.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-300x130.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-768x332.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-1536x663.jpg 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f3-2048x884.jpg 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"263\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-1024x263.jpg\" class=\"attachment-large size-large\" alt=\"Fig. 3. Biophysical characterization of compounds 1\u20134 binding to VHL.\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-1024x263.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-300x77.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-768x197.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-1536x395.jpg 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f4-2048x526.jpg 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure><figure class='gallery-item'>\n\t\t\t<div class='gallery-icon landscape'>\n\t\t\t\t<a href='https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5.jpg'><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"511\" src=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-1024x511.jpg\" class=\"attachment-large size-large\" alt=\"Fig. 4. Co-crystal structures of compounds 1\u20134 in complex with VBC.\" srcset=\"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-1024x511.jpg 1024w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-300x150.jpg 300w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-768x384.jpg 768w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-1536x767.jpg 1536w, https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-content\/uploads\/sites\/233\/2025\/01\/f5-2048x1023.jpg 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a>\n\t\t\t<\/div><\/figure>\n\t\t<\/div>\n\n","protected":false},"excerpt":{"rendered":"<p>The article is a contribution to the journal\u2019s Special Issue for the 2018 Tetrahedron Young Investigators Award for Matthew Fuchter. Read our article Open Access Congratulations Pedro and Xavi, well done! The article is a contribution to the journal\u2019s Special Issue for the 2018 Tetrahedron Young Investigators Award for Matthew Fuchter. Read our article Open [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[19],"tags":[],"class_list":["post-3942","post","type-post","status-publish","format-standard","hentry","category-19"],"blocksy_meta":[],"_links":{"self":[{"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/posts\/3942","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/comments?post=3942"}],"version-history":[{"count":2,"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/posts\/3942\/revisions"}],"predecessor-version":[{"id":4869,"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/posts\/3942\/revisions\/4869"}],"wp:attachment":[{"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/media?parent=3942"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/categories?post=3942"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/sites.dundee.ac.uk\/alessio-ciulli\/wp-json\/wp\/v2\/tags?post=3942"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}