Boc-L-Glutamic acid

Synthesis

The benzyl ester of the amino acid derivative dissolved in methanol was hydrogenated on 10% Pd-C under a hydrogen atmosphere at 1 atm (less than 10% by weight of the amino acid benzyl ester or ether). After the reaction was complete, the catalyst was filtered off, and the filtrate was evaporated under vacuum to give the desired product. BOC-L-glutamic acid can be prepared from commercially available N-tert-butoxycarbonyl-L-glutamic acid benzyl ester (1.0 g, 3.0 mmol). The crude product was purified by rapid chromatography using 30% AcOEt/CH2Cl2/1% AcOH to obtain the desired product. BOC-L-glutamic acid, a white powder (680 mg, 93% yield).

Chemical Properties

white to off-white crystalline powder

Uses

N-Boc-L-glutamic acid is an N-Boc-protected form of L-Glutamic acid (G596960). L-Glutamic acid is a nonessential amino acid that is important to the mammalian central nervous system. L-Glutamic acid is also a neurotransmitter for cone photoreceptors in the human brain and is used as a treatment for patients who have liver disease accompanied by encephalopathy (a condition termed ‘hepatic coma’).

reaction suitability

reaction type: Boc solid-phase peptide synthesis