Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine.

ABSTRACT: We previously reported the synthesis of the 1,N²-deoxyguanosine adducts of 4-hydroxynonenal, an important product of lipid peroxidation, which involved the nucleophilic aromatic substitution reaction of an O⁶-protected-2-fluoroinosine with 4-amino-1,2,5-trihydroxydecanal followed by periodate oxidation of the vicinal diol.³ An improved synthesis of the amino triols has been developed. The syn and anti diasteromers of a key intermediate, 4-nitro-5-hydroxy-1-decene, were synthesized by a Henry reaction and separated; each diastereomer was further separated into individual enantiomers by chiral supercritical fluid chromatography. Of note, dihydroxylation of the terminal olefin under conventional conditions with catalytic OsO_4</

SUBMITTER: Christov PP 

PROVIDER: S-EPMC3735235 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature