<i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids

<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: Kuen Hee Eom, Seokhyeon Baek, Il Kim
Formato: article
Lenguaje:EN
Publicado: MDPI AG 2021
Materias:
amino acids
<i>N</i>-carboxyanhydrides
catalysts
copolymerization
<i>N</i>-heterocyclic carbene
polypeptides
Organic chemistry
QD241-441
Acceso en línea:https://doaj.org/article/62eaa84687584a2b808f3c5be704d3f4
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spelling oai:doaj.org-article:62eaa84687584a2b808f3c5be704d3f42021-11-11T18:43:30Z<i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids10.3390/polym132136742073-4360https://doaj.org/article/62eaa84687584a2b808f3c5be704d3f42021-10-01T00:00:00Zhttps://www.mdpi.com/2073-4360/13/21/3674https://doaj.org/toc/2073-4360Synthetic 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.Kuen Hee EomSeokhyeon BaekIl KimMDPI AGarticleamino acids<i>N</i>-carboxyanhydridescatalystscopolymerization<i>N</i>-heterocyclic carbenepolypeptidesOrganic chemistryQD241-441ENPolymers, Vol 13, Iss 3674, p 3674 (2021)
institution DOAJ
collection DOAJ
language EN
topic amino acids
<i>N</i>-carboxyanhydrides
catalysts
copolymerization
<i>N</i>-heterocyclic carbene
polypeptides
Organic chemistry
QD241-441
spellingShingle amino acids
<i>N</i>-carboxyanhydrides
catalysts
copolymerization
<i>N</i>-heterocyclic carbene
polypeptides
Organic chemistry
QD241-441
Kuen Hee Eom
Seokhyeon Baek
Il Kim
<i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
description 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.
format article
author Kuen Hee Eom
Seokhyeon Baek
Il Kim
author_facet Kuen Hee Eom
Seokhyeon Baek
Il Kim
author_sort Kuen Hee Eom
title <i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
title_short <i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
title_full <i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
title_fullStr <i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
title_full_unstemmed <i>N</i>-Heterocyclic Carbene-Catalyzed Random Copolymerization of <i>N</i>-Carboxyanhydrides of α-Amino Acids
title_sort <i>n</i>-heterocyclic carbene-catalyzed random copolymerization of <i>n</i>-carboxyanhydrides of α-amino acids
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/62eaa84687584a2b808f3c5be704d3f4
work_keys_str_mv AT kuenheeeom iniheterocycliccarbenecatalyzedrandomcopolymerizationofinicarboxyanhydridesofaaminoacids
AT seokhyeonbaek iniheterocycliccarbenecatalyzedrandomcopolymerizationofinicarboxyanhydridesofaaminoacids
AT ilkim iniheterocycliccarbenecatalyzedrandomcopolymerizationofinicarboxyanhydridesofaaminoacids
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