Table 1. 1H (600 MHz) and 13C (150 MHz) NMR Spectroscopic Data for Orfamide N (1) in d3-MeOH.
unit | position | δC, type | δH, mult. [J (Hz)] | unit | position | δC, type | δH, mult. [J (Hz)] |
---|---|---|---|---|---|---|---|
l-Leu1 | 1 | 175.80, C | l-Leu7 | 1 | 172.29, C | ||
2 | 54.29, CH | 4.00, m | 2 | 53.69, CH | 4.47, m | ||
3 | 40.69, CH2 | 1.67, m | 3 | 41.86, CH2 | 1.80, m; 1.47, m | ||
4 | 25.87, CH | 1.69, m | 4 | 25.60, CH | 1.74, m | ||
5 | 22.50, CH3 | 0.95, m | 5 | 21.59, CH3 | 0.90, m | ||
6 | 23.23, CH3a | 0.98, ma | 6 | 23.82, CH3 | 0.96, m | ||
NH | 8.66, brs | NH | 7.94, m | ||||
d-Glu2 | 1 | 176.20, C | l-Leu8 | 1 | 174.95, C | ||
2 | 177.06, C | 2 | 54.34, CH | 4.29, m | |||
3 | 56.55, CH | 4.01, m | 3 | 41.46, CH2 | 1.72, m | ||
4 | 27.32, CH2 | 2.10, m; 2.01, m | 4 | 25.92, CH | 1.67, m | ||
5 | 34.57, CH2b | 2.35, m | 5 | 22.06, CH3 | 0.91, m | ||
NH | 9.41, brs | 6 | 23.37, CH3a | 0.97, ma | |||
NH | 7.90, m | ||||||
d-allo- | 1 | 173.11, C | |||||
Thr3 | 2 | 60.85, CH | 4.30, m | d-Ser9 | 1 | 172.29, C | |
3 | 70.66, CH | 5.38, m | 2 | 57.89, CH | 4.28, m | ||
4 | 18.68, CH3 | 1.39, d (5.9) | 3 | 62.62, CH2 | 3.89, m; 3.81, dd (11.3; 4.2) | ||
NH | 8.20, d (7.2) | NH | 8.04, brs | ||||
d-allo- | 1 | 175.19, C | l-Val10 | 1 | 170.94, C | ||
Ile4 | 2 | 62.62, CH | 3.87, m | 2 | 59.69, CH | 4.33, m | |
3 | 37.06, CH | 2.05, m | 3 | 31.46, CH | 2.16, m | ||
4 | 27.01, CH2 | 1.46, m; 1.18, m | 4 | 19.83, CH3 | 0.87, m | ||
5 | 11.77, CH3 | 0.91, m | 5 | 18.95, CH3 | 0.82, d (6.7) | ||
6 | 16.40, CH3 | 0.98, m | NH | 7.68, m | |||
NH | 7.58, brs | ||||||
3′R–OH-hexadec-9-enoic acid | 1′ | 175.02, C | |||||
d-Leu5 | 1 | 175.50, C | 2′ | 44.52, CH2 | 2.43, m; 2.40, m | ||
2 | 54.97, CH | 4.17, m | 3′ | 69.89, CH | 4.08, m | ||
3 | 40.89, CH2 | 1.79, m; 1.56, m | 4′ | 38.55, CH2 | 1.50, m | ||
4 | 25.83, CH | 1.79, m | 5′ | 26.62, CH2 | 1.50, m | ||
5 | 21.14, CH3 | 0.87, m | 6′ | 30.46, CH2a | 1.28, ma | ||
6 | 23.69, CH3a | 0.93, ma | 7′ | 30.06, CH2a | 1.36, ma | ||
NH | 7.80, brs | 8′ | 28.17, CH2 | 2.04, m | |||
9′ | 130.92, CH | 5.35, m | |||||
d-Ser6 | 1 | 172.98, C | 10′ | 130.79, CH | 5.35, m | ||
2 | 58.33, CH | 4.37, m | 11′ | 28.17, CH2 | 2.04, m | ||
3 | 62.85, CH2 | 3.95, dd (11.6; 5.7); | 12′ | 30.91, CH2a | 1.28, ma | ||
3.89, m | 13′ | 30.85, CH2a | 1.28, ma | ||||
NH | 7.71, brs | 14′ | 32.95, CH2aa | 1.28, ma | |||
15′ | 23.73, CH2 | 1.31, m | |||||
16′ | 14.46, CH3 | 0.89, m |
These four sets of chemical shifts are interchangeable.
Shift acquired via analysis of HSQC data.