Chirality is an essential property for many biologically relevant molecules, including bio(macro)molecules like sugars, amino acids and their polymers (proteins, polysaccharides, DNA/RNA). Despite the seemingly minute structural difference, enantiomers of drugs can exhibit significant differences in their biological activity such as pharmacology, toxicology, pharmacokinetics, pharmacodynamics, etc. For instance, for the analgesic drug ibuprofen, its S-enantiomer has a higher efficacy than its stereoisomer. In the worst case, a stereoisomer can produce undesired or toxic effects. A notorious example is thalidomide, which was first marketed in 1957 as a racemic mixture, but due to severe teratogenic effects (phocomelia, amelia) caused by its S-enantiomer, it was withdrawn from the market in the 1960. Therefore, the isolation of therapeutically active enantiomers is of utmost importance. Chiral resolution can be achieved, inter alia, by chiral chromatography, in which a chiral compound is immobilized on the surface of the stationary phase. Accordingly, it may appear logical to utilize chiral drug delivery systems to also preferentially interact/solubilize a drug enantiomer of interest. Therefore, synthetic stereoactive polymers, in which repeating units feature chiral centers have attracted some attention. Recent studies on poly(lactide) (PLA), poly(glutamic acid) and poly(leucine) based block copolymers have reported the effect of polymer stereoregularity on the physicochemical and functional properties of their self-assembled nanostructures. Feng et al. investigated micelles based on methoxy-poly(ethylene glycol)-b-poly(L-lactide) micelles (mPEG-b-PLLA, L-micelles) and mPEG-b-poly(D-lactide) micelles (mPEG-b-PDLA, D-micelles) to solubilize the glycosylated antibiotic nocathiacin I (containing multiple chiral centres) and other chiral compounds (containing D-or L-sugars). They observed that the nocathiacin I loaded D-micelles exhibited better loading efficiency and smaller particle size than that of L-micelles. Also, for micelles loaded with other chiral compounds, D-and L-micelles showed a marked difference in particle size, even though the loading efficiency between D-and L-micelles were not significantly different. Hu et al. loaded insulin in stereo multiblock copoly(lactide)s (smb-PLAs) with different stereoregularity. They found that smb-PLAs with a high stereoregularity show much higher insulin loading efficiency than the atactic PLA. However, the effect how polymer stereoregular blocks change the properties such as micellar size, micellar thermodynamic stability, drug loading and cell interaction are generally not broadly investigated and understood, in particular beyond poly(lactide).