An Unconventional Method for Purifying the N-carboxyanhydride Derivatives of γ-alkyl-L-glutamates

Poché, Drew S.; Moore, Michael J.; Bowles, Jennifer L.

doi:10.1080/00397919908086042

Cited by 145 publications

(148 citation statements)

References 7 publications

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“…N ε -(carbobenzoxy)-L-lysine N-carboxyanhydride (Z-L-lysine NCA) and γ-benzyl L-glutmate N-carboxyanhydride (BLG NCA) were synthesized according to the method described by Poché et al (Fuchs-Farthing method). 26 Hexamethylated tris(2-(dimethylamino)ethyl)amine (Me 6 TREN) was synthesized according to method of Ciampolini. 27 Synthesis of 2-Bromo-N-(2-hydroxyethyl)-2-methylpropionamide (BrPA) (1) (Scheme 1.…”

Section: Experimental Methodsmentioning

confidence: 99%

Polypeptide Diblock Copolymers: Syntheses and Properties of Poly(N-isopropylacrylamide)-b-Polylysine

2008

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A hydrolysis-resistant amide-linkage heterofunctional initiator was synthesized and used successfully for polymerization of well-defined rod-coil block copolymers poly(N-isopropylacrylamide)-b-poly(Z-L-lysine) (PNIPAm-b-PZLys) by combination of atom transfer radical polymerization (ATRP) and amine hydrochloride mediated ring-opening polymerization (ROP). The ATRP of NIPAm was carried out at 0°C using CuBr/Me 6 TREN complex in 2-propanol and resulted in narrow polydispersity and high monomer conversion. The amine hydrochlorides have replaced the primary amine in the PNIPAm macroinitiator resulting in a well-controlled ROP of N ε -(carbobenzoxy)-L-lysine N-carboxyanhydride in DMF at 20°C. These amphiphilic block copolymers are able to form universal micelle morphologies of spherical micelles, wormlike micelles, and vesicles by varying the polymer compositions and the helicogenic common solvents. From synchrotron SAXS, WAXS, and TEM results, the PNIPAm-b-PZLys microphase self-assembly morphology in solid state is a hierarchical lamellar-inhexagonal structure. After the protective ε-benzyloxycarbonyl group is removed, the dual stimuli-responsive behaviors of the PNIPAm-b-PLys investigated by nuclear magnetic resonance spectroscopy in aqueous solution resulted in either coil-to-helix or coil-globule transition by changing the environmental condition of elevating the temperature or increasing the pH value.

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Section: Experimental Methodsmentioning

confidence: 99%

Polypeptide Diblock Copolymers: Syntheses and Properties of Poly(N-isopropylacrylamide)-b-Polylysine

2008

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“…First, the monomer, BLG-NCA, was synthesized from the commercially available g-benzyl-L-glutamate using the method as reported. 11 Dissolving the monomer and macroinitiator in DMF, different molecular weighted copolymers were synthesized through ROP by changing the ratio of initiator to monomer under N 2 ow. Successful preparation of block copolymers could be demonstrated from the 1 H NMR spectra and GPC results as illustrated in Fig.…”

Section: Synthesis and Characterization Of Pblg-b-pdms-b-pblg Tribcpsmentioning

confidence: 99%

“…[5][6][7][8][9][10] Poly(g-benzyl-L-glutamate) (PBLG) is one of the most well studied polypeptides which could be easily synthesized by ring-opening polymerization (ROP) of N-carboxyanhydrides (NCA) of amino acids. 11,12 The PBLG-based block copolymers can also be effectively synthesized through ROP method using amino-functionalized macroinitiator. [13][14][15] Moreover, the polypeptide synthesized by ROP in some cases could maintain an amino group at the end of the chain, which provides the possibility of further functionalization.…”

Section: Introductionmentioning

confidence: 99%

A novel self-assembled hybrid organogel of polypeptide-based block copolymers with inclusion of polypeptide-functionalized graphene

Lei

Shi

et al. 2017

RSC Adv.

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Self-assembled hybrid organogels of polypeptides containing block copolymers with the inclusion of polypeptide-functionalized graphene were designed and elaborately prepared, and showed interesting microstructures as well as enhanced mechanical performances. Firstly, a series of peptide-based triblock copolymers (triBCPs),, with different lengths of PBLG helices, were synthesized and characterized. As the length of the PBLG helices increased, the critical gelation concentration of the BDB triBCPs decreased while the gel-sol transition temperature increased. Moreover, the PBLG covalently modified graphene oxide (GO) sheets were successfully incorporated into the BDB organogels in toluene and hybrid organogels were prepared. In the presence of GO sheets, the minimum gelation concentration of the hybrid organogel was slightly lowered, and the hybrid organogels preserved thermoreversibility. In the hybrid gels, the triBCPs still self-assembled into nanoribbon structures and the functionalized GO sheets were well dispersed in the gel medium, which was obviously observed by transmission electron microscopy. In addition, the inclusion of the functionalized graphene greatly enhanced the mechanical performance of the hybrid gels, which was demonstrated by the significant increase of the moduli and the fracture stress of the hybrid gels compared with the corresponding native gels in the rheology experiments.

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“…The γ-benzyl-L-glutamate N-carboxyanhydride (Bn-Glu NCA) was prepared according to a literature procedure. 17 All polymerization reactions were performed in flame-dried glassware employing standard high vacuum techniques.…”

Section: Ii-1-materials and Reagentsmentioning

confidence: 99%

Structure of Polypeptide-Based Diblock Copolymers in Solution: Stimuli-Responsive Vesicles and Micelles

et al. 2005

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Polypeptide-based diblock copolymers forming either well-defined self-assembled micelles or vesicles after direct dissolution in water or in dichloromethane, have been studied combining light and neutron scattering with electron microscopy experiments. The size of these structures could be reversibly manipulated as a function of environmental changes such as pH and ionic strength in water. Compared to other pH-responsive seldassembled systems based on "classical" polyelectrolytes, these polypeptide-based nanostructures present the ability to give a response in highly salted media as the chain conformational ordering can be controlled. This makes these micelles and vesicles suitable for biological applications: they provide significant advantages in the control of the structure and function of supramolecular self-assemblies.

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An Unconventional Method for Purifying the N-carboxyanhydride Derivatives of γ-alkyl-L-glutamates

Cited by 145 publications

References 7 publications

Polypeptide Diblock Copolymers: Syntheses and Properties of Poly(N-isopropylacrylamide)-b-Polylysine

Polypeptide Diblock Copolymers: Syntheses and Properties of Poly(N-isopropylacrylamide)-b-Polylysine

A novel self-assembled hybrid organogel of polypeptide-based block copolymers with inclusion of polypeptide-functionalized graphene

Structure of Polypeptide-Based Diblock Copolymers in Solution: Stimuli-Responsive Vesicles and Micelles

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