Chemical Properties
Light Tan Waxy Solid
Uses
Major metabolite of 5-Methyltetrahydrofolic Acid
Uses
Marker in folate metabolism studies.
Definition
ChEBI: A dipeptide resulting from the formal condensation of the carboxylic acid group of 4-aminobenzoic acid with the amino group of L-glutamic acid.
Biological Activity
N-p-Aminobenzoyl)-L-glutamic acid is a folate catabolite th at can be metabolized by bacterial p-aminobenzoate auxotrophs possessing the enzyme p-aminobenzoyl-glutamate hydrolase.
Synthesis
General procedure for the synthesis of N-(4-aminobenzoyl)-L-glutamic acid from N-p-nitrobenzoylglutamic acid: 27.23 g (0.1 mol) of N-nitrobenzoyl-L-glutamic acid and 118 g of methanol were added to a reaction vessel, and stirred until complete dissolution. Subsequently, 0.59 g of 10% Pd/C catalyst was added and 18.92 g (0.3 mol) of ammonium formate was added slowly. The reaction mixture was stirred at room temperature and kept for 30 minutes. After completion of the reaction, the Pd/C catalyst was recovered by filtration. The filtrate was adjusted to pH=3 with hydrochloric acid in methanol and left to stand for 30 min before filtering the precipitated crystals. The crystals were washed with a small amount of methanol and dried to give 25.75 g of N-(4-aminobenzoyl)-L-glutamic acid, with 99.88% purity by HPLC, 96.58% yield, and 95.64% total yield as nitrobenzoic acid.
Purification Methods
Crystallise the acid from H2O. Also purify it by dissolving 2.7g in H2O (130mL), adding aqueous NaOH to pH 5.5 and adding portionwise a solution of 0.5M CuSO4 to complete precipitation of the Cu salt. This salt is filtered off, suspended in H2O and H2S is bubbled through to precipitate CuS, filter, evaporate and recrystallise the residue from H2O. It has max (H2O) at 273nm. [Backer & Houtman Recl Trav Chim Pays-Bas 70 738, 743 1951, Beilstein 14 IV 1153.]
References
[1] Patent: CN105439895, 2016, A. Location in patent: Paragraph 0029; 0030
[2] Chirality, 2010, vol. 22, # 2, p. 252 - 257
[3] Journal of the Chemical Society, 1949, p. 1401,1404
[4] Yakugaku Zasshi, 1949, vol. 69, p. 457
[5] Chem.Abstr., 1950, p. 3442
