{"id":386,"date":"2017-10-27T13:49:46","date_gmt":"2017-10-27T11:49:46","guid":{"rendered":"https:\/\/sites.unimi.it\/apisgroup\/?p=386"},"modified":"2022-01-21T15:31:53","modified_gmt":"2022-01-21T14:31:53","slug":"tandem-tetrahydroisoquinoline-4-carboxylic-acidb-alanineasanew-construct-able-to-induce-aflexible-turn","status":"publish","type":"post","link":"https:\/\/sites.unimi.it\/apisgroup\/2017\/10\/27\/tandem-tetrahydroisoquinoline-4-carboxylic-acidb-alanineasanew-construct-able-to-induce-aflexible-turn\/","title":{"rendered":"Tandem Tetrahydroisoquinoline-4-carboxylic Acid\/beta-Alanineasa New Construct Able To Induce a Flexible Turn"},"content":{"rendered":"<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-medium wp-image-388\" src=\"https:\/\/sites.unimi.it\/apisgroup\/wp-content\/uploads\/2017\/10\/Tic-300x199.png\" alt=\"\" width=\"300\" height=\"199\" srcset=\"https:\/\/sites.unimi.it\/apisgroup\/wp-content\/uploads\/2017\/10\/Tic-300x199.png 300w, https:\/\/sites.unimi.it\/apisgroup\/wp-content\/uploads\/2017\/10\/Tic.png 345w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/>Tetrahydroisoquinoline-4-carboxylic acid, a constrained <em>beta-<\/em>2-amino acid named <em>beta<\/em>-TIC, wassy in the sised for the first time in enantiopure form .The biocatalytic route applied herein represents one of the few successful examples of enzymatic resolu tion of <em>beta-<\/em>2-aminoacids. Model tetrapeptides, namely, Fmoc-l-Ala-b-TIC-b-Ala-l-Val-OBn (Fmoc = fluorenyl-methyloxycarbonyl, Bn = benzyl), containing both isomers of <em>beta<\/em>-TIC, were prepared. Both computational and NMR spectroscopy studies were performed. Areverse-turn conforma-tion was observed in the case of (R)-<em>beta<\/em>-TIC enantiomer thatwas obtained in 99 %enantiomeric excess by enzymatic res-olution. The <em>beta<\/em>-TIC\/<em>beta<\/em>-Ala construct represents the first example of a flexible turn mimetic containing acyclic and an acyclic <em>beta<\/em>-aminoacid. Furthermore,the presence of an aromatic ring of <em>beta<\/em>-TIC could facilitaten on-covalent interactions to increase the potential of this scaffold for the preparation of protein\u2013protein interaction modulators.<\/p>\n<p><span class=\"current-selection\">DOI<\/span><span class=\"ls57\"><span class=\"current-selection\">:1<\/span><span class=\"ls0\"><span class=\"current-selection\">0.1002\/chem<\/span><span class=\"ls2b current-selection\">.2<\/span><span class=\"current-selection\">01701045<\/span><\/span><\/span><\/p>\n<div class=\"t m1 x15 h7 y1c ff4 fs4 fc1 sc0 ls0 ws0\"><\/div>\n","protected":false},"excerpt":{"rendered":"<p>Tetrahydroisoquinoline-4-carboxylic acid, a constrained beta-2-amino acid named beta-TIC, wassy in the sised for the first time in enantiopure form .The biocatalytic route applied herein represents one of the few successful examples of enzymatic resolu&#46;&#46;&#46;<\/p>\n","protected":false},"author":1,"featured_media":388,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6,5,7],"tags":[],"class_list":["post-386","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-application","category-peptidomimetics","category-amino-acid"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.8 - 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