TABLE 1.
Products formed from substituted biphenyls by whole cells of E. coli DH5α(pTCB 144), which contains the CDO of Pseudomonas sp. strain P51
| Substrate | Relative amt (mol %)a | Adsorbance maxima (nm)b | m/z of prominent ions (relative abundance)c | Chemical shifts (δ; ppm) and coupling constants (J, Hz) | EE (%) | Suggested structure and other properties |
|---|---|---|---|---|---|---|
| 2-Chlorobiphenyl | 90 | 280 | 290, M+ +2 (36); 288, M+ (100); 253 (13); 176 (11); 169 (22); 152 (24); 141 (23) | δH: 2′ = 4.40, 3′ = 4.58, 4′ = 5.89, 5′ = 6.07, 6′ = 6.00, 3–6 = 7.25–7.43 J: 2′, 3′ = 5.8, 2′,4′ = 1.0, 3′,4′ = 2.9, 3′, 5′ = 2.3, 3′, 6′ = 0.5, 4′, 5′ = 9.6, 4′, 6′ = 1.0, 5′,6′ = 5.4 |
NDd | (+)-cis-2′,3′-Dihydroxy-2′,3′-dihydro-2-chlorobiphenyl mp = 118–120° [α]d = +120° |
| 10 | ND | 290, M+ +2, (34); 288, M+ (100); 253 (16); 176 (18); 169 (22); 141 (28) | NDd | cis-Dihydroxydihydro-2-chlorobiphenyle | ||
| 3-Chlorobiphenyl | 100 | 303 | 290, M+ +2 (32); 288, M+ (100); 253 (28); 204 (19); 188 (10); 176 (29); 169 (25); 152 (44); 141 (57) | δH: 2′ = 4.35, 3′ = 4.47, 4′ = 5.84, 5′ = 6.04, 6′ = 6.42, 2,4–6 = 7.25–7.59 J: 2′, 3′ = 2.7, 4′,5′ = 9.7, 4′,6′ = 0.9, 5′,6′ = 5.6 | NDd | (+)-cis-2′,3′-Dihydroxy-2′,3′-dihydro-3-chlorobiphenyl mp = 135°C [α]d = +135° |
| 4-Chlorobiphenyl | 100 | 303 | 290, M++2 (31); 288, M+ (100); 253 (29); 204 (30); 188 (15); 176 (32); 169 (27); 152 (47); 141 (58) | >98 | (+)-cis-2′,3′-Dihydroxy-2′,3′-dihydro-4-chlorobiphenyl | |
| mp = 136–139°C | ||||||
| [α]d = +119° | ||||||
| 2-Aminobiphenyl | 100 | 280 | 269, M+ (12); 212 (88); 185 (20); 169 (23); 168 (100); 167 (61) | >98 | cis-Dihydroxydihydro-2-aminobiphenyle | |
| 2-Hydroxybiphenyl | 100 | 294 | 342, M+ (8); 269 (35); 258 (15); 242 (65); 73 (100) | ND | cis-Dihydroxydihydro-2-hydroxybiphenyle | |
| 3-Hydroxybiphenyl | ND | 288 | 342, M+ (17); 269 (42); 258 (19); 242 (69); 73 (100) | ND | cis-Dihydroxydihydro-3-hydroxybiphenyle | |
| ND | 305 | 342, M+ (18); 269 (43); 258 (18); 242 (65); 73 (100) | ND | cis-Dihydroxydihydro-3-hydroxybiphenyle | ||
| 4-Hydroxybiphenyl | 100 | 310 | 342, M+ (19); 269 (43); 258 (18); 242 (67); 73 (100) | ND | cis-Dihydroxydihydro-4-hydroxybiphenyle | |
| 4-Biphenyl carbonitrile | 100 | 248 | 279, M+ (100); 222 (25); 195 (55); 179 (28); 167 (87); 151 (27) | ND | 4-(cis-Dihydroxy-cyclohexadienyl)-benzonitrilee |
a
Relative to the total amount of products; calculated by integration of GC-MS chromatograms (TIC, m/z = 90 to 400). ND, not determined.
b
By HPLC diode array.
c
The m/z values of the prominent ions of the mass spectra of the BB derivatives are given. Additionally, hydroxybiphenyldihydrodiols were derivatized with TMS. Relative abundance, in parentheses, is given as a percentage.
d
GC-MS analysis of the BB derivatives gave a single peak. Since no standards were available, the EE could not be determined.
e
Exact isomeric structure unknown.