title: Controlled synthesis of (S,S)-2,7-diaminosuberic acid: a method for regioselective construction of dicarba analogues of multicystine-containing peptides.
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.
authors.affiliation: School of Chemistry, P.O. Box 23, Monash University, Victoria 3800, Australia.
authors.forename: Jomana
authors.initials: J
authors.lastname: Elaridi
authors.forename: Jim
authors.initials: J
authors.lastname: Patel
authors.forename: W Roy
authors.initials: WR
authors.lastname: Jackson
authors.forename: Andrea J
authors.initials: AJ
authors.lastname: Robinson
mesh_terms: D002210:Caprylates / Q000138:chemical synthesis*; D002384:Catalysis; D003553:Cystine; D003959:Diamines / Q000138:chemical synthesis*; D003998:Dicarboxylic Acids / Q000138:chemical synthesis*; D005998:Glycine / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*; D012238:Rhodium; D012428:Ruthenium; D013237:Stereoisomerism
chemical_list: D002210:Caprylates; D003959:Diamines; D003998:Dicarboxylic Acids; D010455:Peptides; D003553:Cystine; C005738:suberic acid; D012428:Ruthenium; D012238:Rhodium; D005998:Glycine