817562-89-3Relevant academic research and scientific papers
Trivalent Gd-DOTA reagents for modification of proteins
Fisher, Martin J.,Williamson, Daniel J.,Burslem, George M.,Plante, Jeffrey P.,Manfield, Iain W.,Tiede, Christian,Ault, James R.,Stockley, Peter G.,Plein, Sven,Maqbool, Azhar,Tomlinson, Darren C.,Foster, Richard,Warriner, Stuart L.,Bon, Robin S.
, p. 96194 - 96200 (2015/11/24)
The development of novel protein-targeted MRI contrast agents crucially depends on the ability to derivatise suitable targeting moieties with a high payload of relaxation enhancer (e.g., gadolinium(III) complexes such as Gd-DOTA), without losing affinity
Development of a multigram asymmetric synthesis of 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester, (R)-tert-Bu4-DOTAGA1
Levy, Stuart G.,Jacques, Vincent,Zhou, Kevin Li,Kalogeropoulos, Shirley,Schumacher, Kelly,Amedio, John C.,Scherer, Jonathan E.,Witowski, Steven R.,Lombardy, Richard,Koppetsch, Karsten
experimental part, p. 535 - 542 (2010/04/22)
A process for the multigram asymmetric synthesis of the chiral tetraazamacrocycle 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl- 1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester ((R)-tert-Bu4-DOTAGA, 4) has been devised and demonstrated. The nine-step synthesis features an improved synthesis of 2-(S)-5- oxotetrahydrofuran- 2-carboxylic acid, tert-butyl ester 8, the precursor to the novel alkylating agent (S)-5-benzyl 1-tert-butyl 2-(methylsulfonyloxy) pentanedioate 12, which was used to introduce an orthogonally protected chiral glutarate arm to the 1,4,7,10-tetraazacyclododecane (cyclen) nucleus in high optical purity. Cyclen derivative (R)-t-Bu4-DOTAGA, 4, a key intermediate for the manufacture of a magnetic resonance imaging (MRI) candidate, was produced with high chemical (≥95%) and optical (ee ≥ 97%) purity. The process developed was successfully applied to the kilogram-scale cGMP synthesis of (R)-t-Bu4-DOTAGA.
Optically pure and enriched isomers of chelating ligands and contrast agents
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Page/Page column 14; 16; sheet 1; 2, (2008/06/13)
Organic chelating ligands, organic chelating ligand precursors, and metal chelates are disclosed. Methods for synthesizing the same are also described, including methods for preparing optically-enriched or optically-pure compositions of the same.
