Table 1.
NMR Spectroscopic Data (CDCl3 + d4-MeOH (9:1)) for Spiruchostatin C (2)
| position | δC,a type | δH (J in Hz) | HMBCb | |
|---|---|---|---|---|
| Met-sul.c | 1 | 170.9, C=O | 2, 3, NH, NH′ | |
| 2 | 55.8, CH | 4.15, m | 4 | |
| 3 | 24.5, CH2 | 2.33, m | 2, 4 | |
| 2.51, m | ||||
| 4 | 50.4, CH2 | 2.87, m | 2, 3, 5 | |
| 5 | 38.4, CH3 | 2.70, s | 4 | |
| NH | 8.88, br d | |||
| Cys | 1′ | 169.3, C=O | 2′, 3′, 4″, NH″ | |
| 2′ | 55.5, CH | 4.84, m | 3″ | |
| 3′ | 39.6, CH2 | 3.10, m | ||
| 3.28, m | ||||
| NH′ | 6.92, d (8.5) | |||
| Ahhpd | 1″ | 171.7, C=O | 2″, 3″ | |
| 2″ | 40.0, CH2 | 2.62, m | 3″, 4″ | |
| 2.70, m | ||||
| 3″ | 67.9, CH | 4.63, dt (9.4, 3.7) | 2″, 4″ | |
| 4″ | 61.6, CH | 3.00, ddd (9.4, 7.3, 5.5) | 3″, 5″, 6″, 8″ | |
| 5″ | 36.4, CH | 2.09, m | 3″, 4″, 6″, 7″ | |
| 6″ | 27.3, CH2 | 1.24, m | 4″, 5″, 7″, 8″ | |
| 1.56, m | ||||
| 7″ | 11.6, CH3 | 0.92, t (7.5) | 5″, 6″, 8″ | |
| 8″ | 15.4, CH3 | 0.93, d (7.0) | 4″, 5″, 6″ | |
| NH″ | 7.53, d (7.0) | |||
| OH″ | ||||
| Acyl | 1‴ | 172.1, C=O | 2, 2‴, NH | |
| 2‴ | 40.6, CH2 | 2.67, m | 4‴ | |
| 3.21, dd (12.5, 7.0) | ||||
| 3‴ | 71.2, CH | 5.52, br s | 2‴, 4‴ | |
| 4‴ | 130.5, CH | 5.89, d (15.0) | 2‴ | |
| 5‴ | 132.1, CH | 6.10, m | 2‴ | |
| 6‴ | 32.0, CH2 | 2.44, m | 4‴ | |
| 2.65, m | ||||
| 7‴ | 41.8, CH2 | 2.71, m | ||
| 3.39, m |
a
δC determined by 2D experiments
b
HMBC correlations, optimized for 8 Hz, are from proton(s) stated to the indicated carbon
c
Methionine sulfoxide
d
AHHP: 4-amino-3-hydroxy-5-methylheptanoic acid