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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.
Highlights
Since the discovery of the ring-opening polymerization of N-carboxyanhydrides (ROP NCAs) more than one century ago [1] a huge amount of work has been carried out to fabricate polypeptides with different functionalities as well as with variable architectures
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)
The copolymerization of γ-benzyl-L-glutamate NCA (BLG-NCA), N-benzyloxycarbonyl-L-lysine NCA (ZLL-NCA), or L-leucine NCA (Leu-NCA) with VSCys-NCA using 1,1,1-trimethyl-N-2-propenylsilanamine (TMPS) as an initiator proceeded smoothly in DMF at 40 ◦C, yielding P(BLG-co-VSCys), P(ZLL-co-VSCys), or P(Leu-co-VSCys) with defined situ forming polypeptide hydrogels through Michael-type addition chemistry under mild conditions (Figure 22)
Summary
Since the discovery of the ring-opening polymerization of N-carboxyanhydrides (ROP NCAs) more than one century ago [1] a huge amount of work has been carried out to fabricate polypeptides with different functionalities as well as with variable architectures. The advances in the polymerization methodologies enabling the control over the chain length, distribution together with the “living” character of the ROP allow us to fabricate more sophisticated polymeric structures This strategy, known as pre-assembly, resort to the synthetic tools to fabricate well-defined polymeric and usually branched polypeptides [5].
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