A prodrug system for hydroxylamines based on esterase catalysis.
The synthesis and reactivity of hydroxy hydroxamates as models for a prodrug form of hydroxylamine are described. Gamma-hydroxy hydroxamates were found to enable hydroxylamine release via lactonisation. Hydroxamates were found to undergo esterase catalysed hydrolysis.
Department of Chemistry and Oxford Centre for Molecular Sciences, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Ana
A
Conejo-Garcia
Christopher J
CJ
Schofield
D002384:Catalysis; D004950:Esterases / Q000378:metabolism*; D006868:Hydrolysis; D006898:Hydroxylamines / Q000737:chemistry* / Q000378:metabolism*; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship
D006898:Hydroxylamines; D007783:Lactones; D011355:Prodrugs; D004950:Esterases