Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: mechanism based inhibition of glutamate 1-semialdehyde aminomutase

A short synthesis of each enantiomer of 2,3-diaminopropyl hydrogensulfate is described starting from (2R)- and (2S)-asparagine. The compounds serve as inhibitors for pyridoxal 5′-phosphate-dependent (2S)-glutamate 1-semialdehyde aminotransferase, a target for selective herbicides and antibacterial agents on the tetrapyrrole biosynthetic pathway. The (2R)-enantiomer, as predicted, serves as a potent irreversible inactivator.