A 23-26-carbon chain length range of omega-19 (1'R,2'S) cyclopropane fatty acids, related to mycobacterial mycolic acids, has been prepared. The key cyclopropyl intermediate, (1'R,2'S)-(Z)-1-formyl-2-octadecylcyclopropane, underwent Wittig chemistry with various reagents to provide vinylic precursors, which were selectively reduced to the corresponding saturated omega-19 cyclopropane fatty acids or esters. The 24-carbon omega-19 cyclopropane ester was made by chain elongation of the 23-carbon ester. Saturated and unsaturated chiral cyclopropane acids and esters were assayed, using wall extracts of Mycobacterium smegmatis; the incorporation of 14C-acetate was used to measure inhibition or stimulation of mycolic acid synthesis. Minor inhibition (2-3%) was shown by the 23- and 24-carbon saturated esters; all the other compounds were stimulants. The most effective (38-55%) stimulators of mycolate synthesis were the unsaturated esters with 23- and 26-carbons and the saturated and unsaturated 25-carbon acids.

中文翻译：

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5-（1'R，2'S）-（2-十八烷基环丙-1-基）戊酸酯和其他omega-19手性环丙烷脂肪酸及与分枝杆菌分枝杆菌酸有关的酯的合成及性质。

已经制备了与分枝杆菌分枝杆菌酸有关的omega-19（1'R，2'S）环丙烷脂肪酸的23-26碳链长度范围。关键的环丙基中间体（1'R，2'S）-（Z）-1-甲酰基-2-十八烷基环丙烷经过Wittig化学处理与各种试剂一起提供乙烯基前体，将其选择性还原为相应的饱和omega-19环丙烷脂肪酸或酯。24碳omega-19环丙烷酯是通过23碳酯的链延伸制成的。用耻垢分枝杆菌的壁提取物测定饱和和不饱和手性环丙烷酸和酯。14 C-乙酸酯的掺入用于测量对霉菌酸合成的抑制或刺激。23-碳和24-碳饱和酯显示出较小的抑制作用（2-3％）。所有其他化合物都是兴奋剂。霉菌酸酯合成最有效的（38-55％）刺激物是具有23和26个碳原子的不饱和酯以及饱和和不饱和的25个碳酸。