Target specific small molecules as modulators of drug delivery may play a significant role in the future development of therapeutics. Small molecules can alter the in vivo pharmacokinetics of therapeutic macromolecules leading to more efficient drug delivery with less systemic toxicity. The potential of creating a more effective drug delivery system through glycosylation has led, for instance, to the addition of galactose to increase drug delivery to the liver. However, there are many other monosaccharides with potentially useful targeting properties that require further characterization. Here, we investigate the potential of glycosylation to guide molecular therapies using five different monosaccharides conjugated to human serum albumin (HSA). Additionally, we investigate how the amount of glycosylation may alter the pharmacokinetic profile of HSA. We introduce the use of in vivo near-infrared optical imaging to characterize the effect of differential glycosylation on the pharmacokinetics of macromolecules.