Goren M B, Jiang K S
Chem Phys Lipids. 1979 Oct;25(2):209-24. doi: 10.1016/0009-3084(79)90069-0.
We describe the synthesis of 6 pseudo cord 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. From TDA, several bis-amides ('mirror amide' psi CF) and a diester ('mirror' psi CF) of intermediate to high molecular weight were prepared. These superficially resemble cord facotr, have similar infared 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. The results suggest that (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.
我们描述了6种假结核杆菌因子（psi CF）的合成，它们是天然海藻糖-6,6'-二霉菌酸酯的类似物，但基于通过铂催化氧化从海藻糖获得的二羧酸（TDA）。从TDA制备了几种中等至高分子量的双酰胺（“镜像酰胺”psi CF）和二酯（“镜像”psi CF）。这些表面上类似于结核杆菌因子，具有相似的红外光谱，并且与天然产物一样，有几种在小鼠中具有显著的毒性和肿瘤消退活性；但后者的性质并不依赖于前者。在碳水化合物核心和脂质取代基之间引入六亚甲基二胺“间隔基”会导致生物活性出现奇怪的消除。结果表明（除了“间隔基”效应），碳水化合物和脂质部分之间的共价键类型对于类结核杆菌因子糖脂某些生物活性的表达可能相对不重要。
