1

2

Position

13C

1H (J in Hz)

13C

1H (J in Hz)

α-MeSer

 

 

 

 

1

174.7

 

175.3

 

2

59.5

 

60.0

 

3

62.8

3.89, d (10.4)

62.8

3.88, d (10.2), 3.38, d (10.2)

4

20.6

1.29, s

21.0

1.28, s

2-NH

 

7.90, s

 

7.90, s

γ-OH-Pip

 

 

 

 

5

170.1

 

170.6

 

6

48.5

4.78, m

49.0

4.77, m

7

33.4

2.25, 1.94, m

33.9

2.24, 1.92, m

8

61.3

3.65, m

61.8

3.67, m

9

52.7

2.79, m

53.2

2.78, m

9-NH

 

5.28, dd (11.2. 3.1)

 

5.28, dd (12.3, 3.2)

Pip1

 

 

 

 

10

172.9

 

173.4

 

11

48.4

5.60, m

49.0

5.60, m

12

25.8

1.99, 1.78, m

26.5

1.99, 1.74, m

13

21.3

1.52, 1.42, m

21.8

1.51, 1.43, m

14

46.8

2.98, 2.60, m

47.4

2.98, 2.58, m

14-NH

 

5.15, m

 

5.15, m

Pip2

 

 

 

 

15

172.2

 

172.7

 

16

48.4

5.60, m

49.0

5.60, m

17

25.8

1.99, 1.78, m

26.5

1.99, 1.74, m

18

21.3

1.52, 1.42, m

21.8

1.51, 1.43, m

19

46.8

2.98, 2.60, m

47.4

2.98, 2.58, m

19-NH

 

5.15, m

 

5.15, m

Pip3

 

 

 

 

20

170.7

 

173.1

 

21

48.4

5.60, m

49.0

5.60, m

22

25.8

1.99, 1.78, m

26.5

1.99, 1.74, m

23

21.3

1.52, 1.42, m

21.8

1.51, 1.43, m

24

46.8

2.98, 2.60, m

47.4

2.98, 2.58, m

24-NH

 

5.00, dd (12.5, 3.1)

 

5.00, dd (12.2, 3.4)

a-hydroxylic acid

 

 

 

 

25

174.9

 

175.3

 

26

71.8

4.43, m

72.3

4.40, m

27

37.4

1.71, m

31.0

1.95, m

28

22.7

1.23, 1.00, m

20.5

0.88, d (6.9)

29

12.2

0.79, t (7.5)

 

 

30

16.7

0.87, d (6.8)

16.4

0.70, d (6.9)


13C (150 MHz) and 1H (600 MHz) NMR spectra were taken on a NMR System 600 NB CL in DMSO-d6, and the solvent peak was used as an internal standard (δC 39.5, δH 2.50).
Table 1: 1H and 13C NMR spectral data for JBIR-39 (1) and JBIR-40 (2).