Controlled synthesis of (S,S)-2,7-diaminosuberic acid

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dc.contributor.author Elaridi, Jomana
dc.contributor.author Patel, Jim
dc.contributor.author Jackson, W. Roy
dc.contributor.author Robinson, Andrea J.
dc.date.accessioned 2018-08-30T11:33:37Z
dc.date.available 2018-08-30T11:33:37Z
dc.date.copyright 2006 en_US
dc.date.issued 2018-08-30
dc.identifier.issn 1520-6904 en_US
dc.identifier.uri http://hdl.handle.net/10725/8399
dc.description.abstract A method to facilitate regioselective formation of multiple dicarba isosteres of cystine is described. A sequence of ruthenium-catalyzed cross metathesis and rhodium-catalyzed hydrogenation of nonproteinaceous allylglycine derivatives has been developed to achieve high-yielding and unambiguous formation of diaminosuberic acid derivatives. Allylglycine derivatives readily undergo ruthenium-catalyzed metathesis and hydrogenation to yield diaminosuberic acid derivatives in near quantitative yield. Under the same experimental conditions, prenylglycine was found to be inert to both Grubbs' and Wilkinson's catalyzed metathesis and hydrogenation, respectively, but was readily activated for metathesis via cross metathesis with Z-butene. Subsequent cross metathesis of the metathesis-formed crotylglycine derivative, followed by hydrogenation, yielded the second diaminosuberic acid derivative in excellent yield. en_US
dc.language.iso en en_US
dc.title Controlled synthesis of (S,S)-2,7-diaminosuberic acid en_US
dc.type Article en_US
dc.description.version Published en_US
dc.title.subtitle a method for regioselective construction of dicarba analogues of multicystine-containing peptides en_US
dc.author.school SAS en_US
dc.author.idnumber 201100947 en_US
dc.author.department Natural Sciences en_US
dc.description.embargo N/A en_US
dc.relation.journal The Journal of Organic Chemistry en_US
dc.journal.volume 71 en_US
dc.journal.issue 20 en_US
dc.article.pages 7538-7545 en_US
dc.identifier.ctation Elaridi, J., Patel, J., Jackson, W. R., & Robinson, A. J. (2006). Controlled synthesis of (S, S)-2, 7-diaminosuberic acid: a method for regioselective construction of dicarba analogues of multicystine-containing peptides. The Journal of organic chemistry, 71(20), 7538-7545. en_US
dc.author.email jomana.aridi@lau.edu.lb en_US
dc.identifier.tou http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php en_US
dc.identifier.url https://pubs.acs.org/doi/abs/10.1021/jo0606913 en_US
dc.author.affiliation Lebanese American University en_US

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