{"id":5894,"date":"2021-11-03T07:22:02","date_gmt":"2021-11-03T07:22:02","guid":{"rendered":"https:\/\/cblpatras.gr\/comparison-of-fmoc-trt-and-fmoc-t-bu-amino-acid-protection\/"},"modified":"2021-11-03T07:22:02","modified_gmt":"2021-11-03T07:22:02","slug":"comparison-of-fmoc-trt-and-fmoc-t-bu-amino-acid-protection","status":"publish","type":"post","link":"https:\/\/cblpatras.gr\/el\/comparison-of-fmoc-trt-and-fmoc-t-bu-amino-acid-protection\/","title":{"rendered":"Comparison of Fmoc-(Trt) and Fmoc-(t-Bu) Amino Acid Protection"},"content":{"rendered":"<p>Side chain functionalities in Fmoc solid phase synthesis are routinely protected by mild acid labile protecting groups. The foremost choice among these are t-butyl (t-Bu) and trityl (Trt) based groups. In certain situations, the trityl based groups offer distinct advantages over the t-butyl based groups.<\/p>\n<p>The following advantages occur:<\/p>\n<ul>\n<li>If a side chain derivatized peptide is required, for instance on a Ser or Lys residue, and this side chain is protected with a trityl or modified trityl group, then this can be selectively deprotected in the presence of global side chain protection by t-butyl based groups. The modification of the side chain can then be made.<\/li>\n<\/ul>\n<ul>\n<li>The advantages of using trityl versus t-butyl is clearly shown with a range of model peptides consisting of Ser,Thr,Met,Lys and Trp where t-butyl based groups were compared with trityl groups. The relatively mild acidolysis of the trityl groups gave much purer peptides with these difficult amino acid sequences <sup>(1)<\/sup>.<\/li>\n<\/ul>\n<ul>\n<li>It has also been shown that when making deca-serine and comparing trityl protection to t-butyl for side chain protection, the Fmoc group was difficult to remove in the t-butyl series <sup>(2)<\/sup>. Also in a synthesis of a peptide containing greater than 20 amino acids, there was no Kaiser color obtained when attempting to deprotect a Fmoc-Thr(t-Bu) peptide after approximately 15 residues are in the assembly. This suggests that the Fmoc group had not been removed fully <sup>(3)<\/sup>.<\/li>\n<\/ul>\n<p>These observations show that trityl based side chain protection can be used advantageously over t-butyl based protection in many peptides. Trityl side chain protected Fmoc amino acids including Fmoc-Ser(Trt), Fmoc-Thr(trt) and 25 others are readily available in various quantities, in both the D and L configuration from CBL. Please <a href=\"mailto:service@cblbiopharma.com?subject=Request%20for%20Information\">contact us<\/a> to request more information on CBL technologies or to obtain product information.<\/p>\n<ol>\n<li>Barlos, K. Gatos, D. Koutsogianni, S. <em> Peptide Res<\/em>. <strong>51<\/strong>, 194-200 (1998).<\/li>\n<li>Tong, X. Ichihara, K. Tian, Q. Hong, A. <em>Peptide Revolution:<\/em><em>Genomics, Proteomics, and Therapeutics. <\/em>American Peptide Society, 2003.<\/li>\n<li>Dr. Eric Atherton, unpublished results<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Side chain functionalities in Fmoc solid phase synthesis are routinely protected by mild acid labile protecting groups. The foremost choice among these are t-butyl (t-Bu) and trityl (Trt) based groups. In certain situations, the trityl based groups offer distinct advantages over the t-butyl based groups. The following advantages occur: If a side chain derivatized peptide [&hellip;]<\/p>\n","protected":false},"author":3,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"default","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":"default","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":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}}},"categories":[58],"tags":[],"_links":{"self":[{"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/posts\/5894"}],"collection":[{"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/comments?post=5894"}],"version-history":[{"count":0,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/posts\/5894\/revisions"}],"wp:attachment":[{"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/media?parent=5894"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/categories?post=5894"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/tags?post=5894"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}