The molecular and stereochemical structures of photoproducts generated by UV-irradiation of 4'-hydroxymethyl-4,5',8'-trimethylpsoralen in aqueous solution.
UV irradiation of 4'-hydroxymethyl-4,5',8-trimethyl psoralen (HMT) in aqueous solution yields three major photoproducts. We have isolated and characterized (1) a cyclobutane-bridged dimer in which a cis-syn linkage occurs between the furan end of one HMT moiety and the pyrone end of the other; (2) a cyclobutane-bridged dimer wherein both HMT moieties are linked at their pyrone ends with probable cis-syn configuration; and (3) an isomer of HMT for which we have proposed a structure in which the furan and pyrone ring oxygens assume a para orientation via photoisomerization.
Kao
J P
JP
Department of Molecular and Cell Biology, University of California, Berkeley 94720.
Isaacs
S T
ST
Hearst
J E
JE
D002851:Chromatography, High Pressure Liquid; D011564:Furocoumarins / Q000528:radiation effects*; D010100:Oxygen; D013056:Spectrophotometry, Ultraviolet; D014307:Trioxsalen / Q000031:analogs & derivatives / Q000528:radiation effects*; D014466:Ultraviolet Rays
D011564:Furocoumarins; C016507:hydroxymethyltrioxsalen; D010100:Oxygen; D014307:Trioxsalen