Amino acid N-thiocarboxyanhydride (NTA), the thio-analog of N-carboxyanhydride (NCA), is much more stable than NCA against moisture and heat. The convenient monomer synthesis without rigorous anhydrous requirements makes the ring-opening polymerization of NTA a competitive alternative to prepare polypeptide- or polypeptoid-containing materials with potential of large-scale production.Water-soluble polysarcosines (PSars) with high yields (>90%) and low polydispersities (< 1.2) are synthesized from sarcosine N-thiocarboxyanhydride (Sar-NTA) at 60 oC initiated by poly(ethylene glycol) amine (PEG-NH2). The lengths of PSar segments are controlled by various feed ratios of Sar-NTA to PEG. PEG-b-PSar products are a class of novel double-hydrophilic diblock copolymers. Due to the different solubility of PEG and PSar blocks, PEG-b-PSar polymers stabilize oil-in-water emulsions at nano- and micro-scale, which exhibits promising encapsulation applications in food, cosmetics and drug delivery. They also self-assemble to micelles in organic solvents and demonstrate the potential to carry water-soluble cargos.

Synthesis of PEG-<i>b</i>-polysarcosine copolymers from sarcosine <i>N</i>-thiocarboxyanhydrides

248th National Meeting (2014)

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Synthesis of PEG-b-polysarcosine copolymers from sarcosine N-thiocarboxyanhydrides