<i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
Synthetic polypeptides prepared from <i>N</i>-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 de...
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| Autores principales: | , , |
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| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
MDPI AG
2021
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| Materias: | |
| Acceso en línea: | https://doaj.org/article/62eaa84687584a2b808f3c5be704d3f4 |
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| Sumario: | Synthetic polypeptides prepared from <i>N</i>-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 <span style="font-variant: small-caps;">l</span>-alanine NCA with NCAs of <span style="font-variant: small-caps;">l</span>-glutamic acid 5-benzylester (Bn-Glu NCA), <i>S</i>-benzyl-cysteine (Bn-Cys NCA), <i>O</i>-benzyl-<span style="font-variant: small-caps;">l</span>-serine (Bn-Ser NCA), and <span style="font-variant: small-caps;">l</span>-phenylalanine (Phe NCA) was performed using <i>N</i>-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. The reactivity ratio values estimated using the Kelen and Tüdos method show that poly(Bn-Glu-<i>co</i>-Ala) and poly(Bn-Cys-<i>co</i>-Ala) have random repeating units with rich alternating sequences, whereas poly(Bn-Ser-<i>co</i>-Ala) and poly(Phe-<i>co</i>-Ala) contain a larger proportion of Ala-repeating units than Bn-Ser and Phe in random placement. |
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