Lithium hexamethyldisilazide initiated superfast ring opening polymerization of alpha-amino acid N -carboxyanhydrides
TLDR
Lithium hexamethyldisilazide is used to initiate α-amino acid N-carboxyanhydride polymerizations that is very fast and can be conducted in an open vessel, and rapid synthesis of polypeptide libraries for high-throughput functional screening.Abstract:
Polypeptides have broad applications and can be prepared via ring-opening polymerization of α-amino acid N-carboxyanhydrides (NCAs). Conventional initiators, such as primary amines, give slow NCA polymerization, which requires multiple days to reach completion and can result in substantial side reactions, especially for very reactive NCAs. Moreover, current NCA polymerizations are very sensitive to moisture and must typically be conducted in a glove box. Here we show that lithium hexamethyldisilazide (LiHMDS) initiates an extremely rapid NCA polymerization process that is completed within minutes or hours and can be conducted in an open vessel. Polypeptides with variable chain length (DP = 20–1294) and narrow molecular weight distribution (Mw/Mn = 1.08–1.28) were readily prepared with this approach. Mechanistic studies support an anionic ring opening polymerization mechanism. This living NCA polymerization method allowed rapid synthesis of polypeptide libraries for high-throughput functional screening. Ring-opening polymerizations of α-amino acid N-carboxyanhydrides to form polypeptides are usually sensitive to moisture, slow and can undergo side reactions. Here the authors use lithium hexamethyldisilazide to initiate α-amino acid N-carboxyanhydride polymerizations that is very fast and can be conducted in an open vessel.read more
Citations
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Ring opening polymerization of α-amino acids: advances in synthesis, architecture and applications of polypeptides and their hybrids.
Alicia Rasines Mazo,Stephanie Allison-Logan,Fatemeh Karimi,Fatemeh Karimi,Nicholas Jun-An Chan,Wenlian Qiu,Wei Duan,Neil M O'Brien-Simpson,Greg G. Qiao +8 more
TL;DR: Key architectures obtained through NCA ROP or in combination with other polymerization methods are reviewed, as these play an important role in the wide range of applications towards which polypeptides have been applied.
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Dealing with the Foreign-Body Response to Implanted Biomaterials: Strategies and Applications of New Materials
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Aqueous Ring‐Opening Polymerization Induced Self‐Assembly (ROPISA) of N‐carboxyanhydrides
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References
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