TABLE 2.
Products formed from substituted benzenes by whole cells of E. coli DH 5α(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 | Suggested structure |
|---|---|---|---|---|
| 1,2,3-Trichlorobenzene | 100 | 277 | 284, M++4 (11); 282, M++2 (35); 280, M+ (37); 247 (46); 245 (81); 210 (9); 198 (100); 196 (23); 133 (32) | 1,2,3-Trichlorobenzene-cis-dihydrodiolc |
| 1,2,4-Trichlorobenzene | 100 | 283 | 284, M+ +4 (30); 282, M+ +2 (99); 280, M+ (100); 247 (45); 245 (74); 212 (10); 210 (39); 133 (96); 57 (24) | 1,2,4-Trichlorobenzene-cis-dihydrodiold |
| 1,2,3,4-Tetrachlorobenzene | 100 | ND | 318, M+ +4 (9); 316, M+ +2 (17); 314, M+, (15); 281 (60); 279 (61); 246 (38); 244 (68); 218 (50); 216 (100); 57 (76) | cis-1,2-Dihydroxy-3,4,5,6-tetrachlorocyclohexa-3,5-diene |
| Benzonitrile | 88 | 282 | 203, M+ (57); 119 (77); 103 (100); 91 (67); 76 (60) | cis-Dihydroxy cyclohexadienecarbonitriled |
| 12 | ND | 203, M+ (67); 146 (25); 119 (77); 103 (100); 91 (67) | ||
| Benzyl chloride | 100 | 257 | 228, M+ +2 (34); 226, M+ (100); 191 (46); 177 (27); 169 (30); 142 (36); 134 (23); 107 (69); 91 (28); 79 (22) | cis-Dihydroxydihydrobenzyl chlorided |
| Benzyl cyanide | 98.8 | 262 | 217, M+ (20); 191 (39); 177 (51); 160 (36); 134 (70); 117 (61); 107 (100); 91 (90); 77 (61) | 1-(cis-1,2-Dihydroxy-3,5-cyclohexadienyl)-acetonitrilee |
| 0.6 | ND | 217, M+ (22); 191 (36); 177 (52); 160 (36); 117 (68); 107 (100); 91 (79); 77 (56) | 2-(cis-2,3-Dihydroxy-4-6-cyclohexadineyl)-acetonitrilee | |
| 0.6 | ND | 217, M+ (17); 191 (43); 177 (61); 160 (49); 117 (50); 107 (100); 91(93); 77 (52) | 3-(cis-3,4-Dihydroxy-1,5-cyclohexadienyl)-acetonitrilee | |
| Diphenylmethane | 100 | 267 | 268, M+ (84); 191 (53); 184 (28); 177 (57); 121 (40); 91 (100) | cis-Dihydroxydihydrodiphenymethaned |
a
Relative to the total amount of products; calculated by integration of GC-MS chromatograms (total ion current, m/z = 90 to 400).
b
By HPLC. ND, not determined.
c
The m/z values of the prominent ions of the mass spectra of the BB derivatives are given. Relative abundance, in parentheses, is given as a percentage.
d
Exact isomeric structure unknown.
e
Any of the benzyl cyanide products may have one of these structures.