TABLE 1.
One- and two-dimensional NMR spectral data for compounds 1 and 2 in CDCl3
| Position | Compound 1 (5-cis-3-oxo-C12-HSL)
|
Compound 2 (5-cis-C12-HSL)
|
||||
|---|---|---|---|---|---|---|
| 13Ca,c δ (ppm) | 1Hb,c δ (ppm) (multiplicity, J [Hz]) | COSYb,d | HMBCb,e | 13Ca,c δ (ppm) | 1Ha,c δ (ppm) (multiplicity, J [Hz]) | |
| 2 | 174.7 (Cf) | 175.5 (C) | ||||
| 3 | 49.0 (CH) | 4.58 (m) | 4a/b | 49.3 (CH) | 4.57 (m) | |
| 4a/b | 29.9 (CH2) | 2.76 (m), 2.25 (m) | 3, 5a/b | 2, 3 | 30.7 (CH2) | 2.89 (m), 2.18 (m) |
| 5a/b | 66.0 (CH2) | 4.48 (t, 8.8), 4.28 (m) | 4a/b | 2, 3 | 66.1 (CH2) | 4.49 (t, 8.4), 4.31 (m) |
| 1′ | 166.2 (C) | 173.6 (C) | ||||
| 2′ | 47.3 (CH2) | 3.51 (s) | 1′, 3′ | 35.5 (CH2) | 2.28 (t, 7.3) | |
| 3′ | 204.5 (C) | 25.3 (CH2) | 1.73 (p, 7.3) | |||
| 4′ | 42.6 (CH2) | 3.28 (d, 7.0) | 5′ | 3′, 5′, 6′ | 26.5 (CH2) | 2.10 (q, 7.3) |
| 5′ | 119.0 (CH) | 5.51 (dt, 9.6, 7.0) | 4′, 6′, 7′ | 128.2 (CH) | 5.36 (m)g | |
| 6′ | 135.3 (CH) | 5.67 (dt, 9.6, 7.0) | 5′, 7′ | 131.3 (CH) | 5.45 (m)g | |
| 7′ | 27.6 (CH2) | 2.03 (q, 7.0) | 5′, 6′ | 5′, 6′, 8′ | 27.3 (CH2) | 2.02 (q, 6.6) |
| 8′ | 29.2 (CH2) | 1.29 (m) | 29.6 (CH2) | 1.29 (m) | ||
| 9′ | 28.9 (CH2) | 1.29 (m) | 29.0 (CH2) | 1.29 (m) | ||
| 10′ | 31.7 (CH2) | 1.29 (m) | 31.7 (CH2) | 1.29 (m) | ||
| 11′ | 22.6 (CH2) | 1.29 (m) | 12′ | 12′, 10′ | 22.6 (CH2) | 1.29 (m) |
| 12′ | 14.1 (CH3) | 0.88 (t, 7.0) | 11′ | 11′, 10′ | 14.1 (CH3) | 0.90 (t, 7.0) |
a
300/75.5 MHz.
b
500/125.7 MHz.
c
Assignments are based on extensive one- and two-dimensional NMR measurements (HMBC, HSQC, and COSY).
d
Numbers refer to proton resonances.
e
Numbers refer to carbon resonances.
f
Implied multiplicities determined by DEPT.
g
JH5′-H6′ = 10.6 Hz, determined with homonuclear decoupling NMR experiments.