Table 1. 1H and 13C NMR Data for Companeramides A (1) and B (2) in CDCl3 (700 MHz).
companeramide
A (1) |
companeramide
B (2) |
||||||
---|---|---|---|---|---|---|---|
unit | position | δH, mult. (J, Hz) | δC, mult. | unit | position | δH, mult. (J, Hz) | δC, mult. |
AMOYA | 1 | 174.3, C | AMOYA | 1 | 175.4, C | ||
2 | 2.51, dq (7.2, 7.2) | 46.4, CH | 2 | 2.63, m | 46.0, CH | ||
3 | 3.97, m | 51.2, CH | 3 | 3.81, m | 52.4, CH | ||
3-NH | 6.75, br d (6.5) | 3-NH | 7.44, d (6.0) | ||||
4 | 1.71, obs | 31.3, CH2 | 4 | 1.93, m | 30.2, CH2 | ||
1.63, obs | 1.73, m | ||||||
5 | 1.54, m | 25.2, CH2 | 5 | 1.53, m | 25.5, CH2 | ||
1.48, obs | 1.45, m | ||||||
6 | 2.17, obs | 17.9, CH2 | 6 | 2.18, m | 18.0, CH2 | ||
7 | 83.8, C | 7 | 83.4, C | ||||
8 | 1.89, t (2.6) | 68.6, CH | 8 | 1.91, obs | 69.4, CH | ||
9 | 1.31, d (7.5) | 14.2, CH3 | 9 | 1.36, obs | 14.2, CH3 | ||
N-Me-Val-1 | 10 | 170.1, C | N-Me-Val-1 | 10 | 170.2, C | ||
11 | 4.58, d (11.2) | 62.8, CH | 11 | 4.72, d (11.2) | 62.4, CH | ||
12 | 2.29, obs | 25.6, CH | 12 | 2.27, m | 26.5, CH | ||
13 | 0.95, d (6.4) | 19.4, CH3 | 13 | 0.96, obs | 19.9, CH3 | ||
14 | 0.88, d (6.7) | 18.4, CH3 | 14 | 0.81, obs | 18.5, CH3 | ||
15 | 3.14, s | 30.2, CH3 | 15 | 3.23, s | 30.9, CH3 | ||
Ala | 16 | 174.4, C | Val-1 | 16 | 173.4, C | ||
17 | 4.72, obs | 46.2, CH | 17 | 4.58, dd (8.3, 7.8) | 55.5, CH | ||
17-NH | 8.86, d (6.3) | 17-NH | 8.84, d (7.8) | ||||
18 | 1.32, d (7.0) | 16.4, CH3 | 18 | 2.13, m | 30.5, CH | ||
N-Me-Leu | 19 | 169.4, C | 19 | 0.91, obs | 18.8, CH3 | ||
20 | 4.67, dd (9.7, 4.9) | 58.6, CH | 20 | 0.93, obs | 18.7, CH3 | ||
21 | 1.83, ddd (14.5, 8.5, 4.9) | 36.7, CH2 | N-Me-Ala-1 | 21 | 169.8, C | ||
1.59, m | |||||||
22 | 1.41, obs | 24.2, CH | 22 | 4.96, q (6.8) | 56.1, CH | ||
23 | 0.92, d (6.6) | 22.2, CH3 | 23 | 1.32, d (6.8) | 15.3, CH3 | ||
24 | 0.91, d (6.8) | 24.3, CH3 | 24 | 2.74, s | 29.1, CH3 | ||
25 | 2.69, s | 28.8, CH3 | Pro | 25 | 171.8, C | ||
Pro | 26 | 172.4, C | 26 | 4.83, obs | 55.4, CH | ||
27 | 4.92, dd (7.4, 6.4) | 55.4, CH | 27 | 2.10, m | 29.8, CH2 | ||
2.04, m | |||||||
28 | 2.11, m | 29.6, CH2 | 28 | 2.29, m | 25.6, CH2 | ||
2.00, m | 1.97, m | ||||||
29 | 2.28, obs | 25.6, CH2 | 29 | 3.83, m | 48.0, CH2 | ||
1.94, m | 3.72, m | ||||||
30 | 3.84, m | 48.0, CH2 | Ile | 30 | 170.2, C | ||
3.76, dt (9.9, 7.5) | |||||||
Ile-1 | 31 | 170.0, C | 31 | 4.76, m | 54.4, CH | ||
32 | 4.74, dd (8.9, 6.9) | 54.0, CH | 31-NH | 7.48, d (8.5) | |||
32-NH | 6.91, d (8.9) | 32 | 1.70, obs | 39.0, CH | |||
33 | 1.69, obs | 38.6, CH | 33 | 0.93, obs | 15.5, CH3 | ||
34 | 0.92, d (6.5) | 15.4, CH3 | 34 | 1.39, m | 24.7, CH2 | ||
1.06, m | |||||||
35 | 1.39, m | 24.3, CH2 | 35 | 0.87, obs | 11.7, CH3 | ||
1.06, obs | |||||||
36 | 0.83, dd (7.5, 4.8) | 11.0, CH3 | N-Me-Val-2 | 36 | 169.3, C | ||
N-Me-Val-2 | 37 | 169.5, C | 37 | 4.90, d (11.1) | 62.0, CH | ||
38 | 4.71, obs | 61.7, CH | 38 | 2.33, m | 25.8, CH | ||
39 | 2.27, obs | 25.7, CH | 39 | 0.98, obs | 19.9, CH3 | ||
40 | 0.94, d (6.3) | 19.9, CH3 | 40 | 0.78, d (6.5) | 18.7, CH3 | ||
41 | 0.77, d (6.8) | 17.9, CH3 | 41 | 3.06, s | 30.8, CH3 | ||
42 | 3.06, s | 30.5, CH3 | Val-2 | 42 | 172.4, C | ||
Ile-2 | 43 | 172.3, C | 43 | 4.67, dd (9.3, 8.9) | 54.7, CH | ||
44 | 4.72, obs | 53.0, C | 43-NH | 6.80, d (9.3) | |||
44-NH | 6.92, d (8.8) | 44 | 2.00, m | 31.1, CH | |||
45 | 1.74, obs | 37.3, CH | 45 | 0.93, obs | 19.2, CH3 | ||
46 | 0.84, d (6.7) | 15.0, CH3 | 46 | 0.91, obs | 18.4, CH3 | ||
47 | 1.48, obs | 23.4, CH2 | N-Me-Ala-2 | 47 | 170.3, C | ||
1.07, obs | |||||||
48 | 0.82, dd (7.4, 5.0) | 11.0, CH3 | 48 | 5.40, q (7.0) | 52.2, CH | ||
N-Me-Ala | 49 | 170.1, C | 49 | 1.35, obs | 13.8, CH3 | ||
50 | 5.26, q (7.3) | 51.7, CH | 50 | 2.89, s | 30.7, CH3 | ||
51 | 1.31, d (7.3) | 13.5, CH3 | Hiva | 51 | 170.8, C | ||
52 | 2.92, s | 30.5, CH3 | 52 | 4.80, d (7.7) | 75.5, CH | ||
Hiva | 53 | 171.1, C | 53 | 2.19, m | 30.1, CH | ||
54 | 4.80, d (8.3) | 75.4, CH | 54 | 1.08, d (6.9) | 18.2, CH3 | ||
55 | 2.19, obs | 30.1, CH | 55 | 1.00, d (6.5) | 18.2, CH3 | ||
56 | 1.04, d (6.6) | 18.6, CH3 | |||||
57 | 0.93, d (5.7) | 17.8, CH3 |