Table 1.
1H and 13C NMR spectroscopic data for chromomycins A2 (1) and A3 (2).
| Position | 1 | 2 | |||
|---|---|---|---|---|---|
| δH (J in Hz) a | δH (J in Hz) b | δC c | δH (J in Hz) b | δC c | |
| 1 | 202.1 | 202.1 | |||
| 2 | 4.64, d (11.2) | 4.71, d (11.4) | 75.9 | 4.71, d (11.6) | 75.9 |
| 3 | 2.58, m | 2.58, m | 43.7 | 2.67, m | 43.7 |
| 4 | 3.00, d (15.2) | 3.06, d (13.1) | 26.9 | 3.13, m | 26.9 |
| 2.58, m | 2.58, m | 2.67, m | |||
| 5 | 6.58, s | 6.54, s | 100.8 | 6.60, s | 100.7 |
| 6 | 159.6 | 159.6 | |||
| 7 | 111.6 | 111.6 | |||
| 8 | 156.1 | 156.1 | |||
| 9 | 165.3 | 165.2 | |||
| 10 | 6.70, s | 6.66, s | 117.0 | 6.72, s | 117.0 |
| 4a | 134.6 | 134.5 | |||
| 8a | 108.1 | 108 | |||
| 9a | 108.1 | 108 | |||
| 10a | 138.4 | 138.3 | |||
| 7-CH3 | 2.10, s | 2.16, s | 8.2 | 2.16, s | 8.2 |
| 8-OH | 9.74 | 9.78, s | |||
| 9-OH | 15.67 | 15.68, s | |||
| 1′ | 4.67, s | 4.69, br s | 81.8 | 4.70, d (1.6) | 81.9 |
| 2′ | 211.2 | 211.2 | |||
| 3′ | 4.11, d (1.5) | 4.20, br s | 78.2 | 4.21, d (2.0) | 78.2 |
| 4′ | 4.21, qd (6.4, 1.5) | 4.36, q (6.0) | 67.9 | 4.37, qd (6.4, 2.0) | 67.8 |
| 5′ | 1.25 d (6.4) | 1.35, d (6.0) | 20.5 | 1.37, d (6.4) | 20.5 |
| 1′-OCH3 | 3.40, s | 3.49, s | 59.6 | 3.50, s | 59.6 |
| Sugar A | |||||
| A1 | 5.18, d (8.4) | 5.19, d (10.0, 2.0) | 97.3 | 5.21, dd (9.8, 2.1) | 97.3 |
| A2 | 2.16, m | 2.20, m | 32.9 | 2.26, m | 32.9 |
| 2.00, m | 2.02, m | 2.26, m | |||
| A3 | 3.96, m | 3.93, m | 69.9 | 4.00, m | 69.8 |
| A4 | 5.10, d (1.7) | 5.15, d (2.6) | 67.2 | 5.16, d (3.0) | 67.2 |
| A5 | 3.76, m | 3.80, q (6.4) | 69.7 | 3.82, q (6.4) | 69.7 |
| A6 | 1.19, d (6.0) | 1.27, d (6.4) | 16.8 | 1.28, d (6.4) | 16.8 |
| CH3-CO | 2.09, s | 2.15, s | 20.8 | 2.15, s | 20.8 |
| CH3-CO | 170.9 | 170.9 | |||
| Sugar B | |||||
| B1 | 5.05, d (2.8) | 5.10, br s | 95.2 | 5.10, d (2.4) | 95.1 |
| B2 | 1.78, m | 1.63–1.74, m | 33.5 | 1.63–1.75, m | 33.4 |
| 1.64, m | 1.63–1.74, m | 1.63–1.75, m | |||
| B3 | 3.89, dd (7.8, 2.8) | 3.93, m | 65.9 | 3.93, m | 65.8 |
| B4 | 3.14, d (2.8) | 3.21, d (3.2) | 81.5 | 3.21, d (3.2) | 81.5 |
| B5 | 3.82, q (6.5) | 3.93, m | 66.7 | 3.89, q (6.4) | 66.7 |
| B6 | 1.14, d (6.5) | 1.27, d (6.5) | 17.2 | 1.29, d (6.4) | 17.2 |
| B4-OCH3 | 3.51, s | 3.57, s | 62.3 | 3.58, s | 62.3 |
| Sugar C | |||||
| C1 | 5.01, d (9.2) | 5.07, br d (9.7) | 100.3 | 5.08, dd (9.7, 1.6) | 100.3 |
| C2 | 2.46, dd (12.2, 4.6) | 2.49, dd (11.4, 5.2) | 37.4 | 2.49, ddd (12.8, 5.1, 1.6) | 37.4 |
| 1.64, m | 1.63, m | 1.75, m | |||
| C3 | 3.59, m | 3.57, m | 82.3 | 3.59, m | 82.3 |
| C4 | 3.06, d (8.8) | 3.13, d (9.0) | 75.1 | 3.08, m | 75.1 |
| C5 | 3.27, m | 3.38, dq (9.0, 5.5) | 72.1 | 3.32, dq (9.1, 5.5) | 72.1 |
| C6 | 1.28, d (5.6) | 1.34, d (5.5) | 18.0 | 1.34, d (5.5) | 18.0 |
| Sugar D | |||||
| D1 | 4.55, d (9.6) | 4.59, d (9.0) | 99.7 | 4.60, d (9.6, 2.0) | 99.7 |
| D2 | 2.22, dd (11.9, 4.2) | 2.27, dd (13.1, 4.8) | 37.1 | 2.29, dd (5.9, 2.0) | 37.0 |
| 1.56, d (11.9) | 1.63, m | 1.75, m | |||
| D3 | 3.49, m | 3.49, m | 80.7 | 3.47, m | 80.5 |
| D4 | 3.03, d (8.0) | 3.10, d (8.5) | 75.2 | 3.08, m | 75.2 |
| D5 | 3.27, m | 3.30, qd (9.0, 6.0) | 72.3 | 3.40, dq (9.1, 6.0) | 72.2 |
| D6 | 1.31, d (6.0) | 1.37, d (6.0) | 17.8 | 1.38, d (6.0) | 17.8 |
| Sugar E | |||||
| E1 | 4.96 (t, 2.8) | 4.99, dd (3.9, 2.0) | 97.1 | 5.01, dd (4.0, 2.2) | 97.0 |
| E2 | 1.92, m | 2.00, m | 43.8 | 2.00, dd (13.8, 4.0) | 43.6 |
| E3 | 70.6 | 2.06, dd (13.8, 2.2) | 70.6 | ||
| E4 | 4.55, d (9.6) | 4.59, d (9.0) | 79.4 | 4.61, d (9.3) | 79.5 |
| E5 | 3.98, m | 3.88, q (6.7) | 67.0 | 4.00, m | 67.0 |
| E6 | 1.22, d (5.2) | 1.21, d (7.4) | 17.8 | 1.23, d (6.4) | 17.8 |
| E3-CH3 | 1.28, s | 1.33, s | 22.9 | ||
| (CH3)2CH-CO | 1.13, d (6.8) | 1.19, d (7.4) | 19.0 | ||
| (CH3)2CH-CO | 2.58, m | 2.56, m | 34.2 | ||
| (CH3)2CH-CO | 177.5 | ||||
| CH3CO | 2.12, s | 20.9 | |||
| CH3CO | 171.4 | ||||
a Measured at 400 MHz in CDCl3:CD3OD (10:1); b measured at 400 MHz in CDCl3; c measured at 150 MHz in CDCl3.