(+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE - CAS 51268-88-3
Category:
Main Product
Product Name:
(+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE
Catalog Number:
51268-88-3
Synonyms:
CIS-(1R,2S)-1,2-DIHYDRONAPHTHALENE-1,2-DIOL; (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE; (1R,2S)-CIS-1,2-DIHYDRO-1,2-DIHYDROXYNAPHTHALENE; (1R,2S)-CIS-1,2-DIHYDRO-1,2-NAPHTHALENEDIOL; (1R-cis)-1,2-dihydro-1,2-naphthalenediol; (1R-CIS)-1 2-DIHYDRO-
CAS Number:
51268-88-3
Molecular Weight:
162.19
Molecular Formula:
C10H10O2
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1=CC=C2C(C(C=CC2=C1)O)O
InChI:
InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H/t9-,10+/m0/s1
InChIKey:
QPUHWUSUBHNZCG-VHSXEESVSA-N
Chemical Structure
CAS 51268-88-3 (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE

Reference Reading


1.Non-K-region o-quinones as enzyme-generated inactivators of dihydrodiol dehydrogenase.
Penning TM1, Sharp RB, Smithgall TE. Biochemistry. 1989 May 16;28(10):4505-11.
Homogeneous 3 alpha-hydroxysteroid/dihydrodiol dehydrogenase from rat liver cytosol catalyzes the NAD(P)+-dependent oxidation of non-K-region trans-dihydrodiols of polycyclic aromatic hydrocarbons, many of which are proximate carcinogens. These reactions proceed with Km values in the millimolar range to yield highly reactive o-quinones that can be trapped as thioether adducts [Smithgall, T. E., Harvey, R. G., & Penning, T. M. (1988) J. Biol. Chem. 263, 1814-1820]. The enzymatically generated o-quinones, e.g., naphthalene-1,2-dione and benzo[a]pyrene-7,8-dione are potent inhibitors of the dehydrogenase, yielding IC50 values of 5.0 and 10.0 microM, respectively. Naphthalene-1,2-dione was found to be an efficient irreversible inhibitor of the enzyme and can inactivate equimolar concentrations of the dehydrogenase, yielding a t 1/2 for the enzyme of 10 s or less. By contrast (+/-)-trans-1,2-dihydroxy-1,2-dihydronaphthalene promotes a slower inactivation of the dehydrogenase, yielding a Kd of 70 microM and a limiting rate constant that corresponds to a t 1/2 at saturation of 23.
2.Initial reactions in the oxidation of 1,2-dihydronaphthalene by Sphingomonas yanoikuyae strains.
Eaton SL1, Resnick SM, Gibson DT. Appl Environ Microbiol. 1996 Dec;62(12):4388-94.
The substrate oxidation profiles of Sphingomonas yanoikuyae B1 biphenyl-2,3-dioxygenase and cis-biphenyl dihydrodiol dehydrogenase activities were examined with 1,2-dihydronaphthalene and various cis-diols as substrates. m-Xylene-induced cells of strain B1 oxidized 1,2-dihydronaphthalene to (-)-(1R,2S)-cis-1,2-dihydroxy-1,2-3,4-tetrahydronaphthalene as the major product (73% relative yield). Small amounts of (+)-(R)-2-hydroxy-1,2-dihydronaphthalene (15%), naphthalene (6%), and alpha-tetralone (6%) were also formed. Strain B8/36, which lacks an active cis-biphenyl dihydrodiol dehydrogenase, formed (+)-(1R,2S)-cis-1,2-dihydroxy-1,2-dihydronaphthalene (51%), in addition to (-)-(1R,2S)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene (44%) and (+)-(R)-2-hydroxy-1,2-dihydronaphthalene (5%). The cis-biphenyl dihydrodiol dehydrogenase of strain B1 oxidized both enantiomers of cis-1,2-dihydroxy-1,2-dihydronaphthalene, but only the (+)-(1S,2R)-enantiomers of cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene and cis-1,2-dihydroxy-3-phenylcyclohexa-3,5-diene.