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C. Crestini, D. S. Argyropoulos/Bioorg. Med. Chem. 6 (1998) 2161±2169
Table 5. Mass spectrometric data
Product Derivativea MS (m/z) data (%)
1
Ð
274 (M, 100), 241 (24), 227 (21), 199 (19)
1
-Si (CH3)3 418 (M, 38), 403 (M-15, 18), 388 (M-30, 26), 287 (14), 179 (11), 73 (100)
-Si (CH3)3 506 (M, 28), 329 (100), 147 (8), 73 (87)
-Si (CH3)3 432 (M, 21), 417 (M-15, 26), 301 (8), 73 (100)
2
3
4
-Si (CH3)3 446 (M, 12), 431 (M-15, 18), 357 (4), 315 (8), 73 (100)
-Si (CH3)3 476 (M, 16), 373 (7), 358 (10), 147 (14), 73 (100)
5
6
Ð
Ð
Ð
302 (M, 100), 287 (M-15, 16), 272 (M-30, 21) 256 (93), 241 (25), 213 (23), 128 (28)
330 (M, 100), 315 (M-15, 12), 300 (M-30, 18), 284 (96), 269 (27), 241 (22)
288 (M, 84), 255 (21), 241 (8), 151 (33), 138 (100), 123 (7)
7
8
8
-Si (CH3)3 432 (M, 56), 417 (M-15, 12), 402 (M-30, 24), 73 (100)
-Si (CH3)3 520 (M, 9) 505 (M-15, 5), 417 (7), 343 (22), 73 (100)
-Si (CH3)3 446 (M, 28), 431 (M-15, 62), 357 (6), 269 (8), 179 (8), 73 (100)
-Si (CH3)3 490 (M, 13), 431(8), 342 (66), 269 (6), 193 (8), 117 (12), 73 (100)
9
10
11
12
13
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Ð
Ð
316 (M, 100), 301 (M-15, 11), 269 (23), 255 (21), 165 (26), 151 (99), 135 (78)
274 (M, 95), 241 (12), 151 (28), 150 (100), 149 (22), 124 (18), 121 (13)
-Si (CH3)3 419 (M+1, 26), 418 (M, 100), 403 (M-15, 26), 388 (M-30, 91), 358 (23), 343 (18), 179 (20), 73 (81)
-Si (CH3)3 506 (M, 14), 491 (M-15, 4), 476 (M-30, 6), 387 (8), 297 (9), 209 (11), 147 (12), 73 (100)
-Si (CH3)3 432 (M, 22), 414 (M-15, 13), 402 (M-30, 16), 193 (16), 73 (100)
-Si (CH3)3 520 (M, 18), 505 (M-15, 11), 430 (7), 417 (11), 343 (28), 193 (11), 147 (13), 73 (100)
-Si (CH3)3 432 (M, 24), 417 (M-15, 22), 372 (8), 314 (11), 223 (14), 179 (21), 121 (16), 73 (100)
-Si (CH3)3 476 (M, 22), 446 (M-30, 9), 417 (14), 387 (19), 343 (12), 314 (13), 179 (17), 73 (100)
-Si (CH3)3 476 (M, 26), 446 (M-30, 13), 417 (18), 387 (12), 343 (9), 314 (15), 179 (19), 73 (100)
-Si (CH3)3 417 (M+1, 31), 416 (M, 100), 401 (M-15, 4), 386 (M-30, 28), 356 (19), 281 (5), 253 (14), 178 (11), 73 (96)
-Si (CH3)3 432 (M, 6), 417 (M-15, 4), 223 (M-209, 100), 209 (M-223, 12), 179 (21), 165 (9), 73 (32)
-Si (CH3)3 504 (M, 71), 489 (M-15, 6), 474 (M-30, 11), 444 (M-60, 4), 342 (8), 73 (100)
-Si (CH3)3 418 (M, 63), 403 (M-15, 28), 388 (M-30, 25), 373 (M-45, 12), 358 (M-60, 26), 223 (58), 193 (62), 165 (60), 73 (100)
-Si (CH3)3 475 (M+1, 16), 474 (M, 46), 444 (M-30, 8), 356 (18), 253 (6), 73 (100)
Ð
Ð
301 (M+1, 21), 300 (M, 100), 285 (M-15, 39), 225 (16), 210 (14), 210 (9), 181 (14), 152 (15), 139 (14), 128 (16)
316 (M, 5), 302 (36), 271 (24), 227 (12), 207 (16), 165 (100), 137 (22)
-Si (CH3)3 389 (M+1, 11), 388 (M, 69), 373 (M-15, 6), 358 (M-30, 5), 345 (12), 315 (14), 287 (18), 73 (100)
302 (32), 271 (M-31, 24), 227 (14), 207 (16), 165 (100) 137 (19)
Ð
a-: underivatized; -Si (CH3)3: trimethylsilylated with N,O-bis(trimethylsilyl)-acetamide.
2. Bourbonnais, R.; Paice, M. G. Appl. Microbiol. Biotechnol.
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or HBT (1 mM). Oxygen was continously bubbled in the
reaction mixtures. All reactions were conducted in the
dark in order to avoid photochemical oxidation. After
4 h the reactions were halted by heating the mixtures in
boiling water.
3. Bourbonnais, R.; Paice, M. G. FEBS Lett. 1990, 267, 99.
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Acknowledgements
6. Call, H. P. World Patent Application 1994, WO 94/29510.
The authors would like to acknowledge Mr. R. Bour-
bonnais for supplying the puri®ed enzyme used in this
eort, and Dr. F. Archibald for providing constructive
criticism during the writing of this paper. This work was
supported by the Paprican Maintaining Member Com-
panies, and forms a part of a research program under
the auspice of the Protein Engineering Network Centre
of Excellence (PENCE).
7. Bourbonnais, R.; Paice, M. G.; Reid, I. D.; Lanthier, P.;
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