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. Author manuscript; available in PMC: 2010 Apr 1.
Published in final edited form as: Planta Med. 2009 Feb 12;75(5):528–533. doi: 10.1055/s-0029-1185332

Table 2.

NMR data for largamides B (2) and C (3) in DMF-d7 (500 MHz)

Largamide B (2) Largamide C (3)
Unit C/H no. δH (J in Hz) δC, mult. HMBCa δH (J in Hz) δC, mult. HMBCa
Ahppab/Ahphac 1 171.7, qC 171.7, qC
2 4.65, ddd (9.5, 9.5, 5.5) 51.1, CH 1, 3, 4 4.61, ddd (9.5, 9.0, 5.0) 51.2, CH 1, 3, 4, 4a
3 1.88, m
1.56, m		 31.2, CH2 2, 4, 5 1.91, m
1.57, m		 31.4, CH2 5
4 1.60, m
1.58, m		 27.9, CH2 2, 3, 5, 6 1.36, m 25.6, CH2
4ac – – 1.47, m
1.53, m		 32.0, CH2 2, 3, 5
5 2.56, m
2.48, m		 34.7, CH2 3, 4, 6, 7 2.43, m 35.1, CH2 4, 4a, 6, 7/11
6 133.1, qC 133.4, qC
7/11 7.01, d (8.5) 129.9, CH 5, 6, 8/10, 9 7.01, d (8.5) 129.7, CH 5, 8/10, 9
8/10 6.73, d (8.5) 115.7, CH 6, 7/11, 9 6.74, d (8.5) 115.6, CH 6, 9
9 156.5, qC 156.4, qC
OH 9.29, sd 9.28, s 8/10, 9
NH 7.65, d (9.5) 1, 1 (Glu) 7.64, d (9.5)
Glu 1 171.6, qC 171.6, qC
2 4.50, ddd (10.0, 9.0, 5.0) 53.2, CH 1, 3, 4, 1 (Abu) 4.52, ddd (10.0, 8.5, 4.5) 53.1, CH 1, 3, 4, 1 (Abu)
3 2.51, m
2.18, m		 27.0, CH2 2, 4, 5 2.50, m
2.17, m		 27.0, CH2 1, 2, 4, 5
4 2.59, m
2.47, m		 31.0, CH2 2, 3, 5 2.57, m
2.46, m		 31.0, CH2 2, 3, 5
5 175.1, qC 175.1, qC
OH 12.51, br s not observed
NH 7.50, d (9.0) 1 (Abu) 7.51, d (8.5) 2, 1 (Abu)
Abu 1 164.1, qC 164.0, qC
2 131.1, qC 130.9, qC
3 6.55, qd (7.0, 1.0) 129.2, CH 1, 4 6.56, qd (7.0, 1.5) 129.2, CH 1, 4
4 1.77, d (7.0) 12.7, CH3 1, 2, 3 1.76, d (7.0) 12.5, CH3 1, 2, 3
NH 10.16, s 1, 1 (Ala) 10.16, s 1, 1 (Ala)
Ala 1 175.8, qC 175.7, qC
2 4.30, qd (7.0, 2.5) 50.7, CH 1, 3 4.32, qd (7.0, 2.5) 50.6, CH 1, 3
3 1.37, d (7.0) 16.8, CH3 1, 2 1.38, d (7.0) 16.7, CH3 1, 2
NH 8.83, d (2.5) 1, 2, 3 8.85, d (2.5) 1, 2, 3
Thr 1 170.4, qC 170.3, qC
2 4.73, dd (8.5, 2.5) 56.0, CH 1, 1 (Tyr) 4.73, dd (8.5, 3.0) 55.8, CH 1, 1 (Tyr)
3 5.37, qd (6.5, 2.5) 73.4, CH 1, 4, 1 (Ahppa) 5.38, qd (6.5, 3.0) 73.3, CH 1, 1 (Ahpha)
4 1.18, d (6.5) 16.2, CH3 2, 3 1.18, d (6.5) 16.1, CH3 2, 3
NH 7.96, d (8.5) 2, 1(Tyr) 7.91, d (8.5) 2, 1 (Tyr)
Tyr 1 172.8, qC 172.7, qC
2 4.79, ddd (10.0, 8.5, 4.5) 55.5, CH 1, 3, 4, 1 (Val) 4.78, ddd (10.0, 8.0, 4.5) 55.5, CH 1, 4, 1 (Val)
3 3.07, dd (–14.0, 4.5)
2.82, dd (–14.0, 10.0)		 38.2, CH2 1, 2, 4, 5/9 3.07, dd (–14.0, 4.5)
2.82, dd (–14.0, 10.0)		 38.0, CH2 1, 2, 4, 5/9
4 128.6, qC 128.5, qC
5/9 7.11, d (8.5) 131.0, CH 6/8, 7 7.11, d (8.5) 131.0, CH 3, 6/8, 7
6/8 6.70, d (8.5) 115.6, CH 5/9, 7 6.70, d (8.5) 115.6, CH 5/9, 7
7 157.1, qC 157.0, qC
OH 9.34, sd 9.35, s 6/8, 7
NH 8.09, d (8.5) 1, 2, 1 (Val) 8.08, d (8.0) 1, 1 (Val)
Val 1 172.0, qC 172.0, qC
2 4.28, dd (8.5, 7.0) 59.2, CH 1, 3, 4, 5, 1 4.28, dd (8.5, 7.0) 59.2, CH 1, 3, 4, 5, 1(Tig)
(Tig)
3 2.01, m 31.6, CH 1, 2, 4, 5 2.01, m 31.5, CH 1, 2, 4, 5
4 0.74, d (7.0) 19.8, CH3 2, 3, 5 0.74, d (7.0) 19.6, CH3 2, 3, 5
5 0.71, d (7.0) 18.3, CH3 2, 3, 4 0.72, d (7.0) 18.2, CH3 2, 3, 4
NH 7.25, d (8.5) 1, 2, 1 (Tig) 7.26, d (8.5) 1, 2, 1 (Tig)
Tig 1 169.3, qC 169.3, qC
2 132.7, qC 132.6, qC
3 6.42, qq (6.7, 1.5) 130.4, CH 1, 4, 5 6.42, qd (7.0, 1.0) 130.4, CH 1, 4, 5
4 1.71, dq (6.7, 1.5) 13.8, CH3 2, 3 1.71, dq (7.0, 1.0) 13.7, CH3 2, 3
5 1.79, br s 12.6, CH3 1, 2, 3 1.80, br s 12.4, CH3 1, 2, 3
a

Protons showing long-range correlation with indicated carbon.

b

Refers to compound 2.

c

Refers to compound 3.

d

No HMBC observed. Assigned by comparison of data for 2 with data for 1 and 3.