TABLE 2.

¹H-NMR chemical shifts (δ_H, ppm) of ring cleavage intermediates involved in aerobic or anaerobic testosterone catabolic pathways in S. denitrificans cells

1H	3,17-DHSA	2,3-SAOA
1	6.99 (1H, d, J = 8.0 Hz)	−
2	6.59 (1H, dd, J = 8.0, 2.8 Hz)	2.18 (3H, s)
3	−	−
4	6.66 (1H, d, J = 2.8 Hz)	1.88 (1H, m)
		1.73 (1H, m)
5	−	2.31 (1H, m)
6	2.66 (1H, ddd, J = 13.2, 4.8, 4.8 Hz)	1.78 (1H, m)
	2.43 (1H, m)	1.23 (1H, m)
7	1.79 (1H, m)	1.98 (1H, m)
	1.58 (1H, m)	1.73 (1H, m)
8	2.41 (1H, m)	1.36 (1H, m)
9	−	1.47 (1H, m)
10	−	−
11	2.52 (1H, m)	1.62 (1H, m)a
	2.37 (1H, m)	1.25 (1H, m)
12	2.02 (1H, ddd, J = 6.8, 6.0, 2.0 Hz)	1.74 (1H, m)
	1.53 (1H, m)	1.08 (1H, td, J = 13.2, 4.0 Hz)
13	−	−
14	1.61 (1H, m)	1.03 (1H, m)
15	1.71 (1H, m)	1.38 (1H, m)a
	1.51 (1H, m)	0.90 (1H, m)
16	2.19 (1H, m)	1.75 (1H, m)
	1.65 (1H, m)	1.03 (1H, m)
17	3.76 (1H, t, J = 8.4 Hz)	3.57 (1H, t, J = 8.7 Hz)
18	1.10 (3H, s)	0.70 (3H, s)
19	2.25 (3H, s)	0.92 (3H, s)

^aThe signals of H-11 and H-15 of 2,3-SAOA are undistinguishable.