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Eight new diacid amides of dicholesteryl l(d)-alaninates were designed and prepared. The compounds with spacers containing three, four, five, or six carbon atoms and l-alanine residues are denoted as 1a, 2a, 3a, and 4a, respectively, and those containing d-alanine residues are denoted as 1b, 2b, 3b, and 4b, respectively. A gelation test revealed that a subtle change in the length of the spacer and an inverse in the chirality of the amino acid residue can produce a dramatic change in the gelation behavior of the compounds and the microstructures of the gels, as revealed by SEM, XRD, and CD measurements. Importantly, for the compounds 1 and 2, those containing d-alanine residues (1b, 2b) are more efficient gelators than their analogues with opposite chirality (1a, 2a). For the compounds of longer spacers (3, 4), however, those containing l-alanine residues (3a, 4a) are superior to the corresponding ones with d …