Beijerinckia sp strain B1 grows with biphenyl as its sole source of carbon
and energy. A mutant, strain 88/36, oxidized biphenyl to cis-(2S,3R)-dihydr
oxy-1-phenylcyclohexa-4,6-diene (cis-biphenyl dihydrodiol). Strain 88/36 ox
idized anthracene, phenanthrene, benz[a]anthracene and benzo[a]pyrene to ci
s dihydrodiols. Other substrates oxidized to cis-dihydrodiols were dibenzof
uran, dibenzothiophene and dibenzo-p-dioxin, Biphenyl dioxygenase activity
was observed in cells of Beijerinckia B1 and 88/36 after growth in the pres
ence of biphenyl, m-, p-xylene and salicylate. Recent studies have led to t
he reclassification of Beijerinckia B1 as Sphingomonas yanoikuyae strain B1
. Subsequent biotransformation studies showed that S. yanoikuyae 88/36 oxid
ized chrysene to a bis-cis-diol with hydroxyl substituents at the 3,4- and
9,10-positions. Dihydronaphthalene was oxidized to cis-1,2-dihydroxy-1,2,3,
4-tetrahydronaphthalene, naphthalene, cis-1,2-dihydroxy-1,2-dihydronaphthal
ene and 2-hydroxy-1,2-dihydronaphthalene. Anisole and phenetole were oxidiz
ed to phenol. Thus the S. yanoikuyae biphenyl dioxygenase catalyzes cis-dih
ydroxylation, benzylic monohydroxylation, desaturation and dealkylation rea
ctions. To date, the genes encoding biphenyl dioxygenase have not been clon
ed. However, the nucleotide sequence of a S. yanoikuyae B1 DNA fragment con
tains five different alpha subunits as determined by conserved amino acids
coordinating iron in a Rieske [2Fe-2S] center and mononuclear iron at the c
atalytic site. The specific role of the different putative oxygenases in bi
otransformation reactions catalyzed by S. yanoikuyae is not known and prese
nts an exciting challenge for future studies.