Primary ammonium/tertiary amine-mediated controlled ring opening polymerisation of amino acid N-carboxyanhydrides.
TLDR
Stable commercial primary ammonium chlorides were combined with tertiary amines to initiate the controlled ring opening polymerisation of amino acid N-carboxyanhydrides to yield polypeptides with defined end group structure, predetermined molar mass and narrow molarmass distribution.About:
This article is published in Chemical Communications.The article was published on 2015-10-15 and is currently open access. It has received 43 citations till now. The article focuses on the topics: Tertiary amine & Molar mass distribution.read more
Figures
Fig. 4 Time-conversion plots for the polymerisations of (a) BLG–NCA (100 equiv.) and (b) LLeu–NCA (100 equiv.) in DMF initiated by BnA HCl (1 equiv.), BnA HCl/TEA (1 : 0.5 equiv.), BnA (1 equiv.), and TEA (0.5 equiv.). Monomer conversions were determined by FT-IR spectroscopy (see ESI†); numbers in (a) are the polymer dispersities determined by SEC. 
Fig. 3 Polymerisation of BLG–NCA (150 equiv.) in DMF initiated by PyA HCl/TEA (1 : 0.5 equiv.), paused at 24 h by adding HCl and resumed at 81 h by adding TEA. (a) time-conversion plot, (b) number-average molar mass and dispersities (at 24 h, 81 h, 120 h, and 168 h) determined by SEC. 
Fig. 2 SEC traces (RI in black, UV340nm in purple) of polymerisations of BLG–NCA (150 equiv.) in DMF initiated by (a) PyA HCl/TEA (1 : 1.1) at (top to bottom) 2 h, 6 h, 10 h, 24 h; (b) PyA HCl/TEA (1 : 1.5) at (top to bottom) 2 h, 6 h, 8 h, 24 h; the peak (*) is a high molar mass polystyrene (PS2M, 2 MDa) used as internal standard for calculating the monomer conversion (ESI†). 
Fig. 1 SEC traces of PBLGs obtained during the polymerisations of BLG–NCA (150 equiv.) in DMF initiated by (a) TAB 3HCl (1 equiv.), r.t.; (b) TAB 3HCl (1 equiv.), 50 1C; (c) TAB 3HCl/TEA (1 : 0.5 equiv.), r.t.; and (d) TEA (0.5 equiv.), r.t.; the peak (*) is a high molar mass polystyrene (PS2M; 2 MDa) used as internal standard for calculating the monomer conversion (ESI†).
Citations
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Journal ArticleDOI
High-throughput discovery of organic cages and catenanes using computational screening fused with robotic synthesis
Rebecca L. Greenaway,Valentina Santolini,Michael J. Bennison,Ben M. Alston,Chloe J. Pugh,Marc A. Little,Marcin Miklitz,E. G. B. Eden-Rump,Rob Clowes,A. Shakil,H. J. Cuthbertson,H. Armstrong,Michael E. Briggs,Kim E. Jelfs,Andrew I. Cooper +14 more
TL;DR: Computational screening with high-throughput robotic synthesis is combined to create a hybrid discovery workflow for discovering new organic cage molecules, and by extension, other supramolecular systems that form cleanly in one-pot syntheses.
Journal ArticleDOI
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.
Journal ArticleDOI
Lithium hexamethyldisilazide initiated superfast ring opening polymerization of alpha-amino acid N -carboxyanhydrides
TL;DR: 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.
Journal ArticleDOI
Methacrylate-ended polypeptides and polypeptoids for antimicrobial and antifouling coatings
TL;DR: This dual-functional polymer brush coating can be immobilized on the surface of multiple categories of materials through the mussel-inspired pDA coating, and thus should be widely applicable for combating infection in many classes of bio-medical materials.
Journal ArticleDOI
Poly(α-l-lysine)-based nanomaterials for versatile biomedical applications: Current advances and perspectives.
Maochao Zheng,Miao Pan,Wancong Zhang,Huanchang Lin,Shenlang Wu,Chao Lu,Shijie Tang,Daojun Liu,Jianfeng Cai +8 more
TL;DR: This review aims to summarize the recent advances in PLL-based nanomaterials in these biomedical fields over the last decade by describing the synthesis of PLL and its derivatives and the main text of their recent biomedical applications and translational studies.
References
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Aqueous Self-Assembly of Purely Hydrophilic Block Copolymers into Giant Vesicles
TL;DR: This work has synthesized double hydrophilic block copolymers from polysaccharides and poly(ethylene oxide) or poly(sarcosine) to yield high molar mass diblockCopolymers through oxime chemistry, expecting them to be extraordinarily water permeable systems that would be well suited for use as cellular mimics.
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Self-Assembly of Ball-Shaped Molecular Complexes in Water
TL;DR: A simple and versatile access to spheroidal molecular assemblies with pronounced stability in highly polar solvents, composed of doubly and triply charged complementary building blocks based on ammonium or amidinium cations and phosphonate anions is presented.
Journal ArticleDOI
Preparation of Well-Defined Diblock Copolymers with Short Polypeptide Segments by Polymerization of N-Carboxy Anhydrides
TL;DR: In this paper, the ring-opening polymerization of N-carboxy anhydrides (NCA) of γ-benzyl-L-glutamate and β-benzinyl-l-aspartate was studied in the presence of an ammonium chloride-functionalized poly(ethylene oxide) macroinitiator, which possibly prevents side reactions such as NCA deprotonation.
Journal ArticleDOI
From competition to cooperation: a highly efficient strategy towards well-defined (co)polypeptides
TL;DR: A novel highly active organocatalytic system proceeding by an accelerated amine mechanism through monomer activation (AAMMA) and leading to living ROP of α-amino acid N-carboxyanhydrides at room temperature was successfully developed.
Journal ArticleDOI
Polymerization of α‐amino acid N‐carboxyanhydrides catalyzed by rare earth tris(borohydride) complexes: Mechanism and hydroxy‐endcapped polypeptides
TL;DR: In this article, rare earth tris(borohydride) complexes have been used to catalyze the ring-opening polymerization of γ-benzyl-L-glutamate N-carboxyanhydride (BLG NCA).
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