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 i s described starting from (2R)- and (2S)-asparagine. The compounds serve as inhibitors for pyridoxal 5'-phosphate-dependent (2S)-glutamate l-semialdeh yde aminotransferase, a target for selective herbicides and antibacterial a gents on the tetrapyrrole biosynthetic pathway. The (2R)-enantiomer, as pre dicted, serves as a potent irreversible inactivator. (C) 2000 Elsevier Scie nce Ltd. All rights reserved.