For carbohydrates, the six tested chiral fingerprints readily distinguished the 32 stereoisomers of α-D-glucopyranose (2), the 1024 stereoisomers of the disaccharide lactose (3), the 528 possible stereoisomers of the non-reducing, C2-symmetrical α-diglucoside trehalose (4), and all but APC distinguished the 16,384 stereoisomers of the aminoglycoside antibiotic validamycin A (5). However, MAP2C, MAP4C and MAP6C were the only fingerprints capable of differentiating the nine possible stereoisomers of the signaling carbocyclic sugar myo-inositol (6), which all gave identical ECFP4C, ECFP6C and APC fingerprints.