Direct Poly(β-alanine) Synthesis via Polycondensation in Ionic Liquids

Zhang, Shaodong; Goncalves, Leslie Dias; Lefèbvre, Hervé; Tessier, Martine; Rousseau, Brigitte; Fradet, Alain

doi:10.1021/mz300264v

Cited by 22 publications

(14 citation statements)

References 42 publications

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“…The guest polymers, PAlas, were prepared by polycondensation of the alanine monomers using triphenyl phosphite as a condensing agent in an ionic liquid, 1‐butyl‐3‐methylimidazolium chloride, according to the literature procedure . The structure and M n value were determined by the 1 H NMR spectra (Figure a).…”

Section: Resultsmentioning

confidence: 99%

“…d ‐Alanine, l ‐alanine, or their equimolar mixture (0.60 g, 6.8 mmol) and triphenyl phosphite (1.8 mL, 6.8 mmol) was mixed in 1‐butyl‐3‐methylimidazolium chloride (1.2 g) and the resulting mixture was heated at 100 °C for 1 h with stirring under argon . To the reaction mixture, methanol (45 mL) was added to precipitate the product, which was isolated by filtration and dried under reduced pressure to give PAlas.…”

Section: Methodsmentioning

confidence: 99%

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Amylose Stereoselectively Includes Poly(d‐alanine) to Form Inclusion Complex in Vine‐Twining Polymerization: A Novel Saccharide–Peptide Supramolecular Conjugate

Gotanda

Yamamoto

Kadokawa

2016

Macro Chemistry & Physics

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In this study, it is found that amylose stereoselectively includes poly( D -alanine) in the polyalanine stereoisomers in vine-twining polymerization to form the corresponding inclusion complex, a novel saccharide-peptide supramolecular conjugate. The vine-twining polymerization is performed by thermostable phosphorylase-catalyzed enzymatic polymerization, which produces amylose, in the presence of poly( D -alanine), poly( L -alanine), or poly( DL -alanine) dispersed in aqueous buffer solvent. The X-ray diffraction and 1 H NMR measurements of the products indicate that the inclusion complex is formed from poly( D -alanine), whereas the systems using the other stereoisomers do not induce the inclusion complexation. The analytical results and the guest exchange experiment suggest the that average molecular ratio of amylose to poly( D -alanine) is 1:1, and the host cavity is partially occupied by the guest.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Amylose Stereoselectively Includes Poly(d‐alanine) to Form Inclusion Complex in Vine‐Twining Polymerization: A Novel Saccharide–Peptide Supramolecular Conjugate

Gotanda

Yamamoto

Kadokawa

2016

Macro Chemistry & Physics

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“…High molecular weight polyimides and polyamides were obtained using RTILs as novel reaction media, without addition of catalyst. Subsequently, RTILs have been reported to be effective solvents and catalysts for a wide range of condensation polymerizations, including polyamides (95,96), polyesters (97,98), polyethers (99)(100)(101), polyurethanes (102), poly(amino acids) (103), and poly(amide imides) (104,105).…”

Section: Condensation Polymerizationmentioning

confidence: 99%

Polymerization in Ionic Liquids

Zhang

Behera

Hong

et al. 2015

Encyclopedia of Polymer Science and Technology

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Room temperature ionic liquids (RTILs) have proved over recent years to be useful and unique reaction media for a variety of chemical reactions. Faster reaction rates and better selectivities are often observed in RTILs as compared to those in common organic solvents. In addition to these advantages, the low volatility, nonflammability, and recycling potential also help RTILs become a preferred alternative reaction medium to meet environmental and other requirements. This is evidenced by the ever increasing number of papers published in this area every year and interesting and important discoveries. When conventional free radical polymerizations are carried out in RTILs, there is an increase in the propagation rate due to the high polarity of the RTIL and a decrease in the termination rate because of the high viscosity of the RTILs, and thus the overall reaction rate is greatly increased along with an increase in molecular weight. For living/controlled polymerization such as atom transfer radical polymerization and radical addition‐fragmentation and transfer, the reactions in RTILs are still controllable with faster reaction rates and easy separation of catalysts and/or ligands from the resulting polymers. Nearly all types of polymerization processes have now been successfully conducted in RTILs, often with advantageous effects.

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“…Poly‐β‐alanine could be synthesized by the following processes: ring‐opening polymerization of β‐propiolactam and its derivatives in the presence of strong bases, polycondensation of β‐alanine in ionic liquid in the presence of triphenyl phosphite at higher temperatures, elimination of HX form a β‐alanine derivative enzymatic catalyzed ring opening polymerization of substituted and unsubstituted β‐lactam and anionic polymerization of acrylamide in the presence of a strong base …”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and in vitro drug release study of 3‐arm poly‐β‐alanine

Kumar

Adhikary

Tungala

et al. 2015

J of Applied Polymer Sci

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Synthesis of three arms star-shaped poly-b-alanine (3-b-ala) based on tri(prop-2-yn-1-yl) benzene-1,3,5-tricarboxylate (TBT) and azido terminated poly-b-alanine (N 3 -P-ala) was performed using click reaction. TBT was synthesized by nucleophilic substitution reaction between propargyl alcohol and 1,3,5-benzenetricarbonyltrichloride. For the first time, N 3 -P-ala was synthesized through anionic polymerization of acrylamide using sodium azide as an initiator. TBT was characterized by FT-IR and 1 HNMR. N 3 -p-ala was characterized by FT-IR, GPC, and 1 HNMR and 3-b-ala was characterized by FT-IR, GPC, 1 HNMR, TGA, and XRD. The synthesized 3-b-ala was used for drug loading and releasing studies. Polymer loaded drug (3-b-ala-D) hybrid was used in in vitro studies of drug (Diclofenac sodium) release in phosphate buffer solution (PBS) at 37 6 0.5 C and pH 7.4. The drug loading and releasing studies were analyzed by UV-visible spectrophotometer. 3-b-ala-D was examined by AFM to analyze the surface morphology and roughness.

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Direct Poly(β-alanine) Synthesis via Polycondensation in Ionic Liquids

Cited by 22 publications

References 42 publications

Amylose Stereoselectively Includes Poly(d‐alanine) to Form Inclusion Complex in Vine‐Twining Polymerization: A Novel Saccharide–Peptide Supramolecular Conjugate

Amylose Stereoselectively Includes Poly(d‐alanine) to Form Inclusion Complex in Vine‐Twining Polymerization: A Novel Saccharide–Peptide Supramolecular Conjugate

Polymerization in Ionic Liquids

Synthesis, characterization, and in vitro drug release study of 3‐arm poly‐β‐alanine

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