{"id":5896,"date":"2021-11-03T07:22:26","date_gmt":"2021-11-03T07:22:26","guid":{"rendered":"https:\/\/cblpatras.gr\/the-abundant-versatility-of-the-4-methoxytrityl-group\/"},"modified":"2021-11-03T07:22:26","modified_gmt":"2021-11-03T07:22:26","slug":"the-abundant-versatility-of-the-4-methoxytrityl-group","status":"publish","type":"post","link":"https:\/\/cblpatras.gr\/el\/the-abundant-versatility-of-the-4-methoxytrityl-group\/","title":{"rendered":"The Abundant Versatility of the 4-Methoxytrityl Group"},"content":{"rendered":"

One of the most versatile cysteine side chain protecting groups in Fmoc based solid phase synthesis is the 4-Methoxytrityl group (Mmt). The protecting group can be very readily introduced onto the cystine (cys) side chain by the reaction with 4-methoxytrityl chloride with cysteine hydrochloride hydrate. The Mmt group is highly acid sensitive (1). Mmt can be completely removed by 1% trifluoroacetic acid (TFA) in dichloromethane (DCM) \/ triethylsilane (TES) (95:5) in thirty minutes.\u00a0 In comparison, only 4-5% of the trityl group is removed under these conditions when using trityl protected cystine.<\/p>\n

When the Mmt protecting group is used in combination with a 2-chlorotrityl resin support and t-butyl side chain protection for other amino acids, the peptide can be removed from the support, the Mmt group removed and the -S-S- bridge and made directly while retaining side chain protection (1)..<\/sub> As a result, it is compatible with other cystine side chain protecting groups such as S-acetamidomethyl (Acm).<\/p>\n

A novel example of the utility of the Mmt protecting group is on a chain cyclisation reaction to form a disulphide. When used in combination with Cys(StBu) in the same chain, this group can be removed by reduction and converted to Cys(5-Npys) derivative by reaction with 2,2\u2033dithiodi(5nitro)pyridine (DTNP). Treatment of the resin with 1% TFA liberates the thiol which then reacts with the activated Cys(5-Npys) to give the disulphide (2)\u00a0.<\/p>\n

Fmoc-Cys(Mmt)OH, as well as Fmoc protected amino acids and loaded resins, <\/strong>are readily available from CBL from the small to large scale. <\/strong>Please <\/strong>contact us<\/strong><\/a> to request more information on CBL technologies, <\/strong>or to obtain product information.<\/strong><\/span><\/p>\n

1.) Barlos, D. Gatos, O. Hatzi, N. Koch, S. Koutsogianni. Int. J. Peptide Protein Res. <\/em>47. 1996, 148-lS3<\/em><\/span><\/p>\n

2.) Amit K. Galande,, Ralph Weissleder, and, Ching-Hsuan Tung Journal of Combinatorial Chemistry<\/em> 2005 7<\/em> (2), 174-177<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"

One of the most versatile cysteine side chain protecting groups in Fmoc based solid phase synthesis is the 4-Methoxytrityl group (Mmt). The protecting group can be very readily introduced onto the cystine (cys) side chain by the reaction with 4-methoxytrityl chloride with cysteine hydrochloride hydrate. The Mmt group is highly acid sensitive (1). Mmt can […]<\/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\/5896"}],"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=5896"}],"version-history":[{"count":0,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/posts\/5896\/revisions"}],"wp:attachment":[{"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/media?parent=5896"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/categories?post=5896"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/cblpatras.gr\/el\/wp-json\/wp\/v2\/tags?post=5896"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}