Table 1:
Laxaphycin B5 (1) and B6 (2) NMR data in CD3OD and/or CD3OH(900 MHz)
| Laxaphycin B5 (1) | Laxaphycin B6 (2) | ||||
|---|---|---|---|---|---|
| Position | δC | δH, mult (J in Hz) | δC | δH, mult (J in Hz) | |
| Ada | 1 | 173.8 | |||
| 2 | 41.4 | 2.48, m (7.1, 14.4) | 41.2 | 2.5, dd (6.6, 14.2) | |
| 2.58, dd (5.6, 14.4) | 2.57 (4.1, 14.2) | ||||
| 3 | 48.5 | 4.19, m | 48.5 | 4.18, m | |
| 4 | 34.8 | 1.54, q (7.4) | 34.7 | 1.56, m | |
| 5 | 27.3 | 1.31, m | 27.4 | 1.34 | |
| 6 | 30.5 | 1.28, m | 30.8 | 1.29 | |
| 7 | 30.5 | 1.28, m | 30.5 | 1.29 | |
| 8 | 32.2 | 1.27, m | 33.1 | 1.28 | |
| 9 | 23.8 | 1.31, m | 23.7 | 1.31, m | |
| 10 | 14.5 | 0.88a | 14.5 | 0.9a | |
| NH | 7.86, d (8.0) | nd | |||
| Ile | 1 | 174.3 | |||
| 2 | 59.9 | 4.31, t (7.8) | 59.8 | 4.34, m | |
| 3 | 37.9 | 1.89, m | 38.0 | 1.9, m | |
| 3-Me | 16.0 | 0.95, d (7.0) | 16.0 | 0.96a | |
| 4 | 26.3 | 1.21, m | 26.3 | 1.2, m | |
| 1.58, m | 1.58, m | ||||
| 5 | 11.6 | 0.91a | 11.6 | 0.91a | |
| NH | 8.23a | nd | |||
| 3-OHLeu1 | 1 | 173.8 | |||
| 2 | 57.0 | 4.58, m | 57.1 | 4.56, d (3.0) | |
| 3 | 77.5 | 3.68, dd (2.4, 8.2) | 77.3 | 3.68, m | |
| 4 | 32.1 | 1.66, m | 32.3 | 1.67, m | |
| 4-Me | 19.7 | 0.9a | 19.2 | 1.02 (6.5) | |
| 5 | 19.7 | 1.01a | 19.8 | 0.91a | |
| 3-OH | nd | nd | |||
| NH | 7.99, d (6.4) | nd | |||
| Val | 1 | 174.1 | |||
| 2 | 61.4 | 4.18, m | 61.4 | 4.07, m | |
| 3 | 31.5 | 2.14, m | 31.6 | 2.07, m | |
| 3-Me | 19.7 | 0.99a | 19.6 | 0.97a | |
| 4 | 19.3 | 1.00a | 19.6 | 0.97a | |
| NH | 7.90, br | nd | |||
| 3-OHLeu2 (1)/Leu (2) | 1 | 173.7 | |||
| 2 | 57.5 | 4.52, d (9.1) | 53.4 | 4.36, m | |
| 3 | 78.0 | 3.62, dd (1.8, 9.1) | 41.6 | 1.6, m | |
| 4 | 32.3 | 1.66, m | 25.9 | 1.68, m | |
| 4-Me | 19.4 | 0.87a | 23.7 | 0.95a | |
| 5 | 19.7 | 1.01a | 21.3 | 0.90a | |
| 3-OH | nd | x | |||
| NH | 8.12, d (8.4) | nd | |||
| Gln | 1 | 174.7 | |||
| 2 | 51.5 | 4.76, dd (5.2, 7.9) | 50.9 | 4.74, t (6.9) | |
| 3 | 27.6 | 1.98, m | 27.8 | 2.04, m | |
| 2.08, m | 2.06, m | ||||
| 4 | 32.2 | 2.27, q (7.8) | 32.3 | 2.25 | |
| 5 | 178.1 | 178.0 | |||
| NH2 | 6.82, b | nd | |||
| 7.47, b | nd | ||||
| NH | 8.05, d (5.2) | nd | |||
| NMeIle | 1 | 172.2 | |||
| 2 | 62.8 | 4.70, d (10.7) | 62.9 | 4.67, m | |
| 3 | 33.4 | 2.08, m | 33.1 | 2.1, m | |
| 3-Me | 16.1 | 0.91a | 16.0 | 0.92a | |
| 4 | 25.5 | 1.00a | 25.6 | 1.01, m | |
| 1.42, m | 1.41, m | ||||
| 5 | 11.0 | 0.87a | 11.0 | 0.88a | |
| N-Me | 31.9 | 3.16, s | 32.3 | 3.2, s | |
| Asn | 1 | 172.8 | |||
| 2 | 51.5 | 4.82, dd (5.7, 7.2) | 51.4 | 4.84, t (6.4) | |
| 3 | 37.1 | 2.7 (7.2, 15.8) | 37.2 | 2.7, dd (7.3, 15.7) | |
| 2.75 (5.7, 15.8) | 2.75 dd (5.5, 15.7) | ||||
| 4 | 175.0 | ||||
| NH2 | 6.9, b | nd | |||
| 7.58, b | nd | ||||
| NH | 8.24a | nd | |||
| Thr1 | 1 | 170.9 | |||
| 2 | 57.5 | 4.59a | 57.5 | 4.63, d (3.5) | |
| 3 | 68.1 | 4.16, m | 68.1 | 4.19, m | |
| 4 | 19.8 | 1.21 | 19.7 | 1.23, d (6.4) | |
| 3-OH | nd | nd | |||
| NH | 7.56, d (6.6) | nd | |||
| Pro | 1 | 174.4 | |||
| 2 | 62.0 | 4.37, dd (6.3, 7.5) | 62.0 | 4.4, t (6.6) | |
| 3 | 30.5 | 1.71, m | 30.5 | 1.76, m | |
| 2.10, m | 2.12, m | ||||
| 4 | 25.8 | 1.90, m | 25.8 | 1.93, m | |
| 1.92, m | |||||
| 5 | 49.2 | 3.72, m | 49.2 | 3.75, m | |
| 3.78, m | 3.79, m | ||||
| Tyr | 1 | 174.1 | |||
| 2 | 57.0 | 4.47, t (7.8) | 57.1 | 4.46, t (8.2) | |
| 3 | 37.5 | 2.88, dd (7.8,14.1) | 37.3 | 2.89, m | |
| 3.05, dd (7.8, 14.1) | 3.05, m | ||||
| 4 | 128.7 | 129.0 | |||
| 5/9 | 131.3 | 7.03, d (8.4) | 131.3 | 7.03, d (8.0) | |
| 6/8 | 116.4 | 6.69, d (8.4) | 116.4 | 6.69, d (8.0) | |
| 7 | 157.7 | 157.5 | |||
| OH | nd | nd | |||
| NH | 8.15, b | nd | |||
| Thr2 | 1 | 172.0 | |||
| 2 | 60.6 | 4.13, m | 60.7 | 4.12, m | |
| 3 | 67.9 | 4.21, m | 67.8 | 4.23, m | |
| 4 | 20.2 | 0.89a | 14.5 | 0.88a | |
| 3-OH | nd | nd | |||
| NH | 7.68, d (8.2) | nd | |||
*
Laxaphycin B6 carbonyl groups not included due to signal overlap
a –
overlapping signal
x –
not in compound
nd –
no detected signal