Synthesis of conformationally constrained diaminodicarboxylic acid derivatives.
Functionally protected forms of three conformationally constrained diaminodicarboxylic acids were synthesized and characterized. 2,2'-Diaminospiro[3.3]heptane-2,2'-dicarboxylic acid, an analogue of diaminopimelic acid, was prepared in racemic form and the structure established by X-ray crystallographic analysis of the methyl ester hydrochloride. trans-1,4-Diaminocyclohexane-1,4-dicarboxylic acid was prepared and its structure established by X-ray crystallographic analysis of the corresponding Cbz-protected ethyl ester. cis- and trans-2,6-diamino-1,2,3,5,6,7-hexahydro-s-indacene-2,6-dicarboxylic acids were synthesized and the structures assigned by X-ray crystallographic analysis of the corresponding Boc-protected ethyl ester and Cbz-protected ethyl ester, respectively.
Department of Chemistry and Biochemistry, University of Arizona, Tucson, Arizona 85721-0041, USA.
Robin A
RA
Weatherhead
Michael D
MD
Carducci
Eugene A
EA
Mash
D018360:Crystallography, X-Ray; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D003998:Dicarboxylic Acids