Pseudo cord factors: Derivatives of α-D-glucopyranuronosyl (1-1) α-D-glucopyranuronoside

摘要: Abstract We describe the synthesis of 6 pseudo cord factors (Ψ CF), analogs natural trehalose-6,6′-dimycolate, but based instead upon dicarboxylic acid (TDA) that is obtained from trehalose by Pt-catalyzed oxidation. From TDA, several bis-amides (‘mirror amide’ Ψ CF) and a diester (‘mirror’ intermediate to high molecular weight were prepared. These superficially resemble factor, have similar infared spectra and, like product, impressive toxicity in mice tumor-regression activity; latter property does not depend former. A curious abrogation biological activities results introduction hexamethylene diamine ‘spacer’ between carbohydrate core lipid substitutents. The suggest (excepting effect) type covalent linkage moieties may be relatively unimportant for expression some cord-factor-like glycolipids.