Boc-Leu-Gly-OH

Chemical Properties

White powder

Uses

N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-leucyl]-glycine is used to prepare aziridinedicarboxylic acid peptides as cysteine protease inhibitors. It is also used to prepare dipeptide monoester prodrugs of floxuridine with enhanced cancer cell growth inhibition.

Synthesis

General procedure for the synthesis of (S)-2-(2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetic acid from (tert-butoxycarbonyl)-L-leucylglycine methyl ester: Compound 9a (2.6 g, 10 mmol) was dissolved in 50 mL of methanol, 1 M NaOH solution (30 mL) was added, and the reaction was stirred for 3 h at room temperature. Upon completion of the reaction, the solvent was removed by vacuum concentration and the pH of the residue was adjusted to 2-3 with 1 M HCl. Subsequently, the mixture was extracted three times with ethyl acetate (EtOAc). The organic phases were combined and dried over anhydrous sodium sulfate (Na2SO4). After filtration, ethyl acetate was evaporated under reduced pressure to give compound 10a as a white solid in 92.4% yield.

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 11, p. 3055 - 3064
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2009, vol. 64, # 2, p. 237 - 244
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 887 - 895