PSEUDO CORD FACTORS - DERIVATIVES OF ALPHA-D-GLUCOPYRANURONOSYL (1-1)ALPHA-D-GLUCOPYRANURONOSIDE

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