Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4.
The stereospecific oxidation of indan and indene was examined with mutant and recombinant strains expressing naphthalene dioxygenase of Pseudomonas sp. strain 9816-4. Pseudomonas sp. strain 9816/11 and Escherichia coli JM109(DE3)[pDTG141] oxidized indan to (+)-(1S)-indanol, (+)-cis-(1R,2S)-indandiol, (+)-(1S)-indenol, and 1-indanone. The same strains oxidized indene to (+)-cis-(1R,2S)-indandiol and (+)-(1S)-indenol. Purified naphthalene dioxygenase oxidized indan to the same four products formed by strains 9816/11 and JM109(DE3)[pDTG141]. In addition, indene was identified as an intermediate in indan oxidation. The major products formed from indene by purified naphthalene dioxygenase were (+)-(1S)-indenol and (+)-(1R,2S)-indandiol. The results show that naphthalene dioxygenase catalyzes the enantiospecific monooxygenation of indan to (+)-(1S)-indanol and the desaturation of indan to indene, which then serves as a substrate for the formation of (+)-(1R,2S)-indandiol and (+)-(1S)-indenol. The relationship of the desaturase, monooxygenase, and dioxygenase activities of naphthalene dioxygenase is discussed with reference to reactions catalyzed by toluene dioxygenase, plant desaturases, cytochrome P-450, methane monooxygenase, and other bacterial monooxygenases.
Gibson
D T
DT
Department of Microbiology, University of Iowa, Iowa City 52242, USA.
Resnick
S M
SM
Lee
K
K
Brand
J M
JM
Torok
D S
DS
Wackett
L P
LP
Schocken
M J
MJ
Haigler
B E
BE
D001572:Benzofurans / Q000378:metabolism; D001673:Biodegradation, Environmental; D049308:Dioxygenases; D004579:Electron Transport; D006900:Hydroxylation; D007189:Indans / Q000378:metabolism*; D007192:Indenes / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism; D009097:Multienzyme Complexes / Q000235:genetics / Q000378:metabolism*; D010105:Oxygenases / Q000235:genetics / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology*; D011994:Recombinant Proteins / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
D001572:Benzofurans; D007189:Indans; D007192:Indenes; D007211:Indoles; D009097:Multienzyme Complexes; D011994:Recombinant Proteins; C093579:1,2-indanediol; C093580:1-indenol; C016515:1-indanol; C093581:indene; C057812:indoline; C043168:coumaran; D010105:Oxygenases; D049308:Dioxygenases; C038703:naphthalene dioxygenase; C093582:indan