3-Aminopentanedioic acid

ChEBI: A 1,5-dicarboxylic acid compound having a 3-amino substituent. It has been isolated from the extracts of the algae, Chondria armata.

Isoglutamic acid is a 1,5-dicarboxylic acid compound having a 3-amino substituent. It has been isolated from the extracts of the algae, Chondria armata. It has a role as a marine metabolite and an algal metabolite. It derives from a glutaric acid. It is a conjugate acid of an isoglutamate(1-).

General procedure: In a glass vial with a screw cap, to a solution of ester 1a-c(0.1 mmol) in 4 mL of phosphate buffer 0.1M pH 7.5, the desired enzyme was added (in the amount specified in Table 1). The mixture wasstirred at room temperature under orbital shaking (700 rpm). The reactionwas monitored at set time intervals with chiral HPLC (reactiontimes specified in Table 1) for evaluate the substrate conversion and theenantiomeric excess of unreacted esters 1a-c. At the end of the reaction, the residual solution was extracted with CH2Cl2 (3×5 mL), dried onanhydrous Na2SO4, filtered and concentrated. The aqueous phase waslyophilized and the ratio of compounds 2/3/4 was analysed via 1HNMR.General procedure: In a glass vial with a screw cap, to a solution of ester 1a-c(0.1 mmol) in 4 mL of phosphate buffer 0.1M pH 7.5, the desired enzyme was added (in the amount specified in Table 1). The mixture wasstirred at room temperature under orbital shaking (700 rpm). The reactionwas monitored at set time intervals with chiral HPLC (reactiontimes specified in Table 1) for evaluate the substrate conversion and theenantiomeric excess of unreacted esters 1a-c. At the end of the reaction, the residual solution was extracted with CH2Cl2 (3×5 mL), dried onanhydrous Na2SO4, filtered and concentrated. The aqueous phase waslyophilized and the ratio of compounds 2/3/4 was analysed via 1HNMR.Preparation of Compound 8d To a solution of beta-glutamic acid (500 mg, 0.339 mmol) in MeOH (10 mL) was added thionyl chloride (0.148 mL, 2.04 mmol) at 0 C under N2. After 24 hours, the reaction mixture was concentrated to produce the compound 8d (697 mg), which was used without further purification. 1H-NMR (400 MHz, CDC13) delta 7.40-7.27 (m, 5H), 5.11 (s, 2H), 3.72 (s, 2H), 3.56 (s, 2H), 2.13 (br s, 1H).To a solution of beta-glutamic acid (500 mg, 0.339 mmol) in MeOH (10 mL) was added thionyl chloride (0.148 mL, 2.04 mmol) at 0 C under N2. After 24 hours, the reaction mixture was concentrated to produce the compound 8d (697 mg), which was used without further purification. 1H-NMR (400 MHz, CDC13) delta 7.40-7.27 (m, 5H), 5.11 (s, 2H), 3.72 (s, 2H), 3.56 (s, 2H), 2.13 (br s, 1H).

Molecular Weight:147.13
XLogP3:-3.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:147.05315777
Monoisotopic Mass:147.05315777
Topological Polar Surface Area:101
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes