A glutamic acid-based polymer keeping intact the integrity of all the three original functionalities of the amino acid

Abstract

Dimethyl glutamate, on treatment with allyl bromide, afforded dimethyl N,N-diallylglutamate which upon alkaline ester hydrolysis followed by acidification with aqueous HCl gave N,N retaining the integrity of all the three functionalities of glutamic acid. Under the influence of pH, the repeating units of triprotic acid (+) in II were equilibrated to those of water-insoluble diprotic polyzwitterionic acid (±) III, water-soluble monoprotic poly(zwitterion-anion) (±−) IV, and its conjugate base polydianion (=) V. The critical salt concentration required to promote water solubility of (±) III has been determined to be 0.548 M NaCl, 0.271 M NaBr, 0.133 M NaI. The basicity constants of the carboxyl groups and trivalent nitrogen in (=) V have been determined. A 5 ppm and 20 ppm concentrations of III are effective in inhibiting the precipitation of CaSO 4 from its supersaturated solution with a ≈100% scale inhibition efficiency at 40 °C for a duration of over 3 and 16 h, respectively.

Simulations and Potentiometric Titrations Enable Reliable Determination of Effective pKa Values of Various Polyzwitterions

“…Synthesis of Poly(N,N-diallyl glutamate) (PDAGA). The synthesis of PDAGA was originally reported by Jamiu et al 38 HCl was introduced to a suspension with 59 g of glutamic acid (0.4 mol) in 500 mL of methanol at 0 °C. Then, the solution was stirred for 3 days.…”

Alternate cyclopolymer of diallylglutamic acid and sulfur dioxide

“…Dimethyl N,N-diallylglutamate (7), synthesized from dimethyl glutamate (6), was hydrolyzed with NaOH and acidi-ed with HCl to obtain N,N-diallylglutamic acid hydrochloride 4 as described. 20…”

“…16 The abundant availability of inexpensive glutamic acid has led us to synthesize and cyclopolymerize [17][18][19] diallylglutamic acid 4 to obtain poly(diallylglutamic acid) 5 which retained all three original functionalities of the amino acid (Scheme 1). 20 Note that the nitrogen in the peptide bond in PGA loses its basic character while retaining only one of the original carboxylate motifs of the amino acid. Glutamic acid and materials derived from it are of tremendous importance for biomedical and material research.…”

Stimuli‐Responsive Macromolecular Architecture by Butler Cyclopolymerizations: Synthesis and Applications

“…As described in Scheme 20, glutamic acid‐derived monomer 126 was polymerized to generate a series of pH‐responsive polymer backbones of 127 – 130 having chelating residues of glutamic acid [82] . PZ 128 was water‐insoluble, while 129 and 130 were found to be water‐soluble.…”