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Synthesis of water-soluble poly(α-hydroxy acids) from living ring-opening polymerization of O-benzyl-L-serine carboxyanhydrides.

ACS macro letters (2013-01-30)
Yanbing Lu, Lichen Yin, Yanfeng Zhang, Zhang Zhonghai, Yunxiang Xu, Rong Tong, Jianjun Cheng
ABSTRACT

O-benzyl-L-serine carboxyanhydrides were synthesized via diazotization of O-benzyl-L-serine with sodium nitrite in aqueous sulfuric acid solution followed by cyclization of the resulting serine-based α-hydroxy acid with phosgene. Degradable, water-soluble poly(α-hydroxy acids) bearing pendant hydroxyl groups were readily prepared under mild conditions via ring-opening polymerization of O-benzyl-L-serine carboxyanhydrides followed by removal of the benzyl group and showed excellent cell compatibility, suggesting their potential being used as novel materials in constructing drug delivery systems and as hydrogel scaffolds for tissue engineering applications.

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Sigma-Aldrich
Phosgene solution, 15 wt. % in toluene