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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http://dx.doi.org/10.1021/mz200165c | DOI Listing |
Polymers (Basel)
October 2021
Department of Polymer Science and Engineering, Pusan National University, Busandaehag-ro 63-2, Geumjeong-gu, Busan 46241, Korea.
Synthetic polypeptides prepared from -carboxyanhydrides (NCAs) of α-amino acids are useful for elucidating the relationship between the primary structure of natural peptides and their immunogenicity. In this study, complex copolypeptide sequences were prepared using a recently developed technique; specifically, the random copolymerization of l-alanine NCA with NCAs of l-glutamic acid 5-benzylester (Bn-Glu NCA), -benzyl-cysteine (Bn-Cys NCA), -benzyl-l-serine (Bn-Ser NCA), and l-phenylalanine (Phe NCA) was performed using -heterocyclic carbene (NHC) catalysts. The NHC-initiated Ala NCA/Bn-Glu NCA and Ala NCA/Bn-Cys NCA copolymerization reactions achieved 90% conversion within 30 min.
View Article and Find Full Text PDFACS Macro Lett
April 2012
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China ; Department of Materials Science and Engineering, University of Illinois at Urbana-Champaign, 1304 W. Green Street, Urbana, IL 61801, USA.
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.
View Article and Find Full Text PDFActa Biomater
April 2011
Department of Fiber Science and Apparel Design, Cornell University, Ithaca, NY 14853, USA.
The synthesis of a new family of biodegradable α-amino acid poly(ester amide)s (AA-PEAs) with pendant benzyl ether groups and hydroxyl functional groups is reported. The synthetic strategy employs the ring opening reaction of O-benzyl-L-serine-N-carboxyanhydride with di-p-toluenesulfonic acid salts of bis-L-valine butane-1,4-diester, followed by solution polycondesation reactions with di-p-nitrophenyl sebacate in N,N-dimethylacetamide. Catalytic hydrogenation of the resulting benzyl ether protected AA-PEAs (PEA-Ser-Bzs) was performed to restore the hydroxyl functional groups in the functionalized AA-PEAs (PEA-Ser-OH).
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