Polypeptides by light: photo-polymerization of N-carboxyanhydrides (NCA)

Stukenkemper, Timo; Jansen, J. F. G. A.; Lavilla, Cristina; Dias, Aylvin A.; Brougham, Dermot F.; Heise, Andreas

doi:10.1039/c6py02018f

Cited by 27 publications

(23 citation statements)

References 38 publications

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“…A novel interesting strategy to fabricate polypeptides was reported by Heise et al [ 81 ]. They reported the first example of UV-initiated synthesis of polypeptides from NCAs.…”

Section: Polymerization Of α-Amino Acid N -Carbmentioning

confidence: 99%

Strategies to Fabricate Polypeptide-Based Structures via Ring-Opening Polymerization of N-Carboxyanhydrides

2017

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Abstract:In this review, we provide a general and clear overview about the different alternatives reported to fabricate a myriad of polypeptide architectures based on the ring-opening polymerization of N-carbonyanhydrides (ROP NCAs). First of all, the strategies for the preparation of NCA monomers directly from natural occurring or from modified amino acids are analyzed. The synthetic alternatives to prepare non-functionalized and functionalized NCAs are presented. Protection/deprotection protocols, as well as other functionalization chemistries are discussed in this section. Later on, the mechanisms involved in the ROP NCA polymerization, as well as the strategies developed to reduce the eventually occurring side reactions are presented. Finally, a general overview of the synthetic strategies described in the literature to fabricate different polypeptide architectures is provided. This part of the review is organized depending on the complexity of the macromolecular topology prepared. Therefore, linear homopolypeptides, random and block copolypeptides are described first. The next sections include cyclic and branched polymers such as star polypeptides, polymer brushes and highly branched structures including arborescent or dendrigraft structures.

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“…A novel interesting strategy to fabricate polypeptides was reported by Heise et al [ 81 ]. They reported the first example of UV-initiated synthesis of polypeptides from NCAs.…”

Section: Polymerization Of α-Amino Acid N -Carbmentioning

confidence: 99%

Strategies to Fabricate Polypeptide-Based Structures via Ring-Opening Polymerization of N-Carboxyanhydrides

2017

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“…We recently disclosed the first example of a light-triggered NCA ring-opening polymerization in solution employing a photoamine generator (PAG). [20] Light-triggered ring-opening polymerization of NCAs and lactones was also reported by Dong [21] and Boyer, [22] respectively. In our process, upon UV irradiation a primary amine is generated which initiates the NCA ring-opening polymerization.…”

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confidence: 64%

“…Primary amines are efficient initiators in NCA polymerization and in our previous work, we identified 4,5‐dimethoxy‐2‐nitrobenzylcyclohexylcarbamate as the most suitable PAG for the polymerization of NCAs . Compared to other investigated PAGs, the absorption spectrum of this compound allowed the use of a blacklight lamp overcoming heat‐triggered side reactions.…”

Section: Resultsmentioning

confidence: 97%

“…An approach that has not been explored to date is light‐induced surface grafting of polypeptides from solid substrates. We recently disclosed the first example of a light‐triggered NCA ring‐opening polymerization in solution employing a photoamine generator (PAG) . Light‐triggered ring‐opening polymerization of NCAs and lactones was also reported by Dong and Boyer, respectively.…”

Section: Introductionmentioning

confidence: 97%

“…">Results and DiscussionPrimary amines are efficient initiators in NCA polymerization and in our previous work, we identified 4,5-dimethoxy-2-nitrobenzylcyclohexylcarbamate as the most suitable PAG for the polymerization of NCAs. [20] Compared to other investigated PAGs, the absorption spectrum of this compound allowed the use of a blacklight lamp overcoming heattriggered side reactions. To enable this process from a surface, the silane-based photoamine generator 3 was synthesized by the reaction of 4,5-dimethoxy-2-nitrobenzyl alcohol 1 with 3-(triethoxysilyl)propyl isocyanate 2 (Scheme 1).…”

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confidence: 99%

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Polypeptide Polymer Brushes by Light‐Induced Surface Polymerization of Amino Acid N‐Carboxyanhydrides

Stukenkemper

Paquez

Verhoeven

et al. 2018

Macromol. Rapid Commun.

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Silicon wafers are decorated with photoamine generator 4,5-dimethoxy-2-nitrobenzyl 3-(triethoxysilyl)propyl carbamate. UV-irradiation in the presence of benzyl-l-glutamate N-carboxyanhydride is carried out, resulting in the release of the surface-bound primary amines, making them viable N-carboxyanhydride (NCA) polymerization initiators. Successful polypeptide grafting is confirmed by water contact angle measurements as well as by ellipsometry, revealing a poly(benzyl-l-glutamate) (PBLG) layer of ≈3 nm. X-ray photoelectron spectroscopy confirms the presence of amide groups in the grafted PBLG while time-of-flight secondary ion mass spectroscopy provides additional evidence for the presence of PBLG on the surface. Evaluation of negative control samples confirms successful UV surface grafting. The approach is thus established as a viable general method for light exposure directable polypeptide functionalization of silicon surfaces.

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Ring‐Opening Polymerization of α‐Amino Acid N ‐Carboxyanhydrides and Side‐Chain Functionalized Polypeptides

Sun

2019

Encyclopedia of Polymer Science and Technology

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Synthetic polypeptides from ring‐opening polymerization of α‐amino acid N ‐carboxyanhydrides (NCA) are versatile materials for various biomedical applications due to their biocompatibility, biodegradability, and bioactivity. This article overviews recent progress in NCA polymerizations and side‐chain functionalization of polypeptides. Initiating systems, mechanism studies, and optimized polymerization conditions for the NCA polymerization are comprehensively reviewed and evaluated here. The substituents of NCA monomers are also described. Finally, the design and synthesis of functional polypeptides is summarized and discussed.

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Polypeptides by light: photo-polymerization of N-carboxyanhydrides (NCA)

Abstract: Synthesis of well-defined synthetic polypeptides by in situ UV-triggered formation of amine initiators.

Cited by 27 publications

References 38 publications

Strategies to Fabricate Polypeptide-Based Structures via Ring-Opening Polymerization of N-Carboxyanhydrides

Strategies to Fabricate Polypeptide-Based Structures via Ring-Opening Polymerization of N-Carboxyanhydrides

Polypeptide Polymer Brushes by Light‐Induced Surface Polymerization of Amino Acid N‐Carboxyanhydrides

Ring‐Opening Polymerization of α‐Amino Acid N ‐Carboxyanhydrides and Side‐Chain Functionalized Polypeptides

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