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. 2015 Jan 6;78(3):413–420. doi: 10.1021/np5007907

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