Chemical Properties
white to light yellow crystal powde
Uses
N2-Fmoc-L-glutamine is an N-Fmoc-protected form of L-Glutamine (G597000). L-Glutamine is a non-essential amino acid that is important for cells that proliferate quickly in the body, such as those of the immune system. L-Glutamine is known to be especially important for the gut, as it helps to maintain intestinal structure and function. L-Glutamine also has protective properties against host toxicity of chemotherapy in cancer patients.
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
Synthesis
To a stirred solution of L-glutamine (1.75 g, 12 mmol) and sodium carbonate (1.27 g, 12 mmol) in 30 mL of water, a solution of 9-fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu, 3.0 g, 8.9 mmol) dissolved in 60 mL of tetrahydrofuran (THF) was slowly added. The reaction mixture was stirred overnight at room temperature. Subsequently, THF was removed by distillation under reduced pressure. the residue was diluted with 100 mL of 1N hydrochloric acid and the precipitated white solid was collected by filtration. The solid was further recrystallized in a mixed aqueous solution of DMF with 0.1 N hydrochloric acid to afford the target product (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoic acid as a white powder (2.76 g, 84% yield). The product was characterized by 1H-NMR (90 MHz, DMSO-d6) with chemical shifts of 12.47 (1H, s), 7.89-7.20 (10H, m), 6.68 (1H, s, br), 4.22-3.90 (4H, m), and 2.25-1.86 (4H, m).
References
[1] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[2] Patent: US2006/161007, 2006, A1. Location in patent: Page/Page column 12
[3] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
