Biodegradable Poly(ester hydrazide)s via Enzymatic Polymerization

Abstract

Summary: The reaction of hydrazine with ethyl glycolate results in 1,2‐bisglycoylhydrazine, a monomer that was used for the lipase‐catalyzed synthesis of biodegradable poly(ester hydrazide)s. The polymers derived from the hydrazide‐containing monomer and vinyl‐activated adipic, suberic, and sebacic acid, respectively, showed low melting temperatures of 136 to 141 °C and are thermally stable up to 300 °C. The aliphatic poly(ester hydrazide)s (PEHs) are highly crystalline, as proven by polarization microscopy and atomic force microscopy. Further, the PEHs represent the first described biodegradable poly(hydrazide)s. They degrade in the presence of lipase at 37 °C within a few weeks.Synthetic route to poly(ester hydrazide)s.imageSynthetic route to poly(ester hydrazide)s.

Polymer Networks Synthesized from Poly(Sorbitol Adipate) and Functionalized Poly(Ethylene Glycol)

“…Alternatively, enzymatic polymerization can be used for the synthesis of functional polyesters with different advantages [ 17 , 18 ]. It has emerged as a versatile technique for green polymer synthesis over more than two decades, and where enzymes work as biocatalysts to drive the chemical reaction [ 19 , 20 , 21 , 22 ]. Thus, it avoids the risk of toxicity which can occur due to metal based catalysts (zinc, aluminum, tin, antimony etc.…”

Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

“…This fact allows to better preserve the regioselectivity of the lipases [ 58,59 ] and synthesis procedures can be easily extended to the usage of polyols as potential monomers for obtaining linear polyesters bearing pendant hydroxyl functional groups. [ 60 ] Additionally, the mild reaction conditions open the possibility of better control the reaction of hydrazide‐ containing monomers, [ 61 ] the construction of epoxide‐containing polyesters, [ 62 ] the efficient production of aromatic polyesters, [ 63 ] and the preparation of reactive polyesters preserving the unsaturated moieties from renewable plant oils for further crosslinking reactions. [ 64 ]…”

Development of Poly(sorbitol adipate)-g-poly(ethylene glycol) Mono Methyl Ether-Based Hydrogel Matrices for Model Drug Release

“…Enzymatic polymerization provides us with one of the alternatives to the abovementioned polymers that utilizes green chemistry to synthesize functional polyesters in which enzymes are being used as biocatalysts [22][23][24][25][26]. The enzymes enable us to produce aliphatic polyesters without exposure to metal-based catalysts that carry toxicity risk in a conventional polymerization process [22].…”