. Author manuscript; available in PMC: 2014 May 1.

Published in final edited form as: Chem Biol Drug Des. 2013 Apr 4;81(5):615–624. doi: 10.1111/cbdd.12107

Table 1.

Summary of the 1H and 13C NMR Data

MTM SA-Glycine methyl ester
Position	δH (J in Hz)	δC, mult.	HMBC
1		216.2, C
2	4.36 (bs, 1H)	78.7, CH
3	2.44 – 2.58 (m, 2H)	45.2, CH
4	2.44 – 2.58 (m, 2H) 2.82, d (11.0)	28.1, CH₂
4a		136.9, C
5	6.22, s	102.0, CH
6		159.8, C
7		111.6, C
7-CH₃	2.10, bs	8.9, CH₃
8		156.7, C
8a		108.6, C
9		164.1, C
9a		109.1, C
10	6.48, s	118.2, CH	102.0, 108.6, 109.1
10a		139.5, C
1'	4.13 (bs, 2H)	81.2, CH	28.1, 45.2, 60.4, 175.2
1'-OCH₃	3.56 (bs, 4H)	60.4, CH₃	81.2
2'		175.2, C
4'	3.99, d (17.5) 4.13 (bs, 2H)	41.8, CH	175.2
5'		171.9, C
5'-OCH₃	3.80 (bs, 5H)	52.9, CH₃	171.9
1A	4.87 (overlap, 1H)	97.3, CH
2A	1.74 – 1.82 (m, 2H) 2.36, bs	38.3, CH₂	100.0
2A	1.74 – 1.82 (m, 2H) 2.36, bs	38.3, CH₂
3A	3.80 (bs, 5H)	80.9, CH
4A	3.07, t (8.5), 2H	76.5, CH	73.3, 80.9
5A	3.36 – 3.48 (m, 3H)	73.3, CH
6A	1.32, d (6.0), 2H	18.8, CH₃	73.3, 76.5
1B	4.63 – 4.80 (m, 2H)	100.0, CH
2B	1.53 – 1.68 (m, 3H) 2.22 (m, 1H)	40.9, CH₂
3B	3.56 (bs, 4H)	72.2, CH
4B	2.98, t (8.8)	78.2, CH	18.4, 72.2, 73.9
5B	3.36 – 3.48 (m, 3H)	73.9, CH
6B	1.35, d (6.0)	18.4, CH₃	73.9, 78.2
1C	4.97 – 5.15 (m, 2H)	102.5, CH
2C	1.53 – 1.68 (m, 3H) 2.62, d (7.5)	38.4, CH₂
3C	3.80 (bs, 5H)	81.2, CH
4C	3.07, t (8.5), 2H	76.7, CH	81.2
5C	3.36 – 3.48 (m, 3H)	73.6, CH
6C	1.42, bs	18.9, CH₃	73.6
1D	4.63 – 4.80 (m, 2H)	100.3, CH
2D	1.74 – 1.82 (m, 2H) 1.89 – 2.01 (m, 2H)	33.3, CH₂
3D	3.89, d (11.5)	77.5, CH
4D	3.71 (bs, 2H)	70.6, CH	77.5
5D	3.63 – 3.68 (m, 1H)	72.2, CH
6D	1.32, d (6.0), 2H	17.3, CH₃	70.6, 72.2
1E	4.97 – 5.15 (m, 2H)	99.1, CH	77.5
2E	1.53 – 1.68 (m, 3H) 1.89 – 2.01 (m, 2H)	45.4, CH₂	99.1
2E	1.53 – 1.68 (m, 3H) 1.89 – 2.01 (m, 2H)	45.4, CH₂	71.9, 78.1
3E		71.9, C
3E-CH₃	1.25, s	27.4, CH₃	45.4, 71.9, 72.0, 78.1
4E	2.93, d (9.5)	78.1, CH	18.9, 72.0
5E	3.71 (bs, 2H)	72.0, CH
6E	1.27, d (6.5)	18.9, CH	71.9, 72.0, 78.1

MTM SA-alanine methyl ester
Position	δH (J in Hz)	δC, mult.	HMBC
1		204.2, C
2	4.42, d (11.5)	78.5, CH
3	2.45 – 2.56 (m, 2H)	45.0, CH
4	2.45 – 2.56 (m, 2H) 2.60 – 2.73 (m, 1H)	28.3, CH₂
4a		136.4, C
5	6.34, s	102.1, CH	108.5, 111.8, 118.1
6		160.1, C
7		111.8, C
7-CH₃	2.09, s	8.9, CH₃
8		156.7, C
8a		108.5, C
9		164.9, C
9a		109.0, C
10	6.45, s	118.1, CH	28.3, 102.1, 108.5, 109.0
10a		139.6, C
1'	4.13, s	81.0, CH	28.3, 45.0, 60.4, 78.5, 174.1
1'-OCH₃	3.59 (bs, 4H)	60.4, CH₃	81.0
2'		174.1, C
4'	4.56, m (7.0)	49.8, CH	17.8, 174.1, 174.4
4'-CH₃	1.52, d (7.0)	17.8, CH₃	49.8, 174.4
5'		174.4, C
5'-OCH₃	3.75, s	53.1, CH₃	174.4
1A	4.94 – 5.13 (m, 3H)	97.6, CH
2A	1.75 – 1.87 (m, 2H) 2.36 – 2.45 (m, 1H)	38.2, CH₂	100.1
2A	1.75 – 1.87 (m, 2H) 2.36 – 2.45 (m, 1H)	38.2, CH₂
3A	3.77 – 3.84 (m, 2H)	81.0, CH
4A	3.03 – 3.12 (m, 2H)	76.5, CH	18.8, 73.4, 81.0
5A	3.44 – 3.52 (m, 1H)	73.4, CH
6A	1.33, d (6.5)	18.8, CH₃	73.4, 76.5
1B	4.65 – 4.78 (m, 2H)	100.1, CH
2B	1.55 – 1.66 (m, 3H) 2.18 – 2.26 (m, 1H)	40.9, CH₂
2B	1.55 – 1.66 (m, 3H) 2.18 – 2.26 (m, 1H)	40.9, CH₂	72.2, 78.3
3B	3.59 (bs, 4H)	72.2, CH
4B	2.98, t (9.0)	78.3, CH	18.4, 72.2, 73.8
5B	3.36 – 3.44 (m, 2H)	73.8, CH
6B	1.34, d (6.5)	18.4, CH₃	73.8, 78.3
1C	4.94 – 5.13 (m, 3H)	102.4, CH
2C	1.55 – 1.66 (m, 3H) 2.60 – 2.73 (m, 1H)	38.5, CH₂	100.3
3C	3.77 – 3.84 (m, 2H)	81.2, CH
4C	3.03 – 3.12 (m, 2H)	76.7, CH	19.0, 73.6, 81.2
5C	3.36 – 3.44 (m, 2H)	73.6, CH
6C	1.39, d (5.5)	19.0, CH₃	73.6, 76.7
1D	4.65 – 4.78 (m, 2H)	100.3, CH	81.2
2D	1.75 – 1.87 (m, 2H) 1.96 – 2.02 (m, 1H)	33.3, CH₂
3D	3.86 – 3.93 (m, 1H)	77.4, CH
4D	3.68 – 3.72 (bs, 2H)	70.6, CH	17.3, 33.3, 77.4
5D	3.65 (m, 1H)	72.2, CH	70.6
6D	1.31, d (6.5)	17.3, CH₃	70.6
1E	4.94 – 5.13 (m, 3H)	99.1, CH	77.4
2E	1.55 – 1.66 (m, 3H) 1.93, d (13.0)	45.4, CH₂	99.1
2E	1.55 – 1.66 (m, 3H) 1.93, d (13.0)	45.4, CH₂	71.9, 78.1, 99.1
3E		71.9, C
3E-CH₃	1.25, s	27.4, CH₃	45.4, 71.9, 78.1, 99.1
4E	2.93, d (10.0)	78.1, CH	18.9, 27.4, 71.9, 72.0
5E	3.68 – 3.72 (bs, 2H)	72.0, CH
6E	1.27, d (6.5)	18.9, CH	72.0, 78.1

MTM SA-valine methyl ester
Position	δH (J in Hz)	δC, mult.	HMBC
1		202.8, C
2	4.53, d (10.0)	78.2, CH
3	2.37 – 2.58 (m, 3H)	45.0, CH
4	2.37 – 2.58 (m, 3H) 2.81 – 2.90 (m, 1H)	28.5, CH₂
4a		136.3 C
5	6.42 (bs, 2H)	102.0, CH
6		160.2, C
7		111.9, C
7-CH₃	2.08 (bs, 3H)	8.9, CH₃
8		156.8, C
8a		108.7, C
9		150.5, C
9a		109.0, C
10	6.42 (bs, 2H)	118.0, CH
10a		139.6, C
1'	4.17, s	81.3, CH	28.5, 45.0, 60.4
1'-OCH₃	3.60 (bs, 5H)	60.4, CH₃	81.3
2'		174.3, C
4'	4.44, d (3.5)	59.1, CH	173.4
5'		173.4, C
5'-OCH₃	3.77 (bs, 5H)	52.9, CH₃	173.4
6’	2.32 (m, 1H)	31.8, CH	19.2, 20.1, 59.1
7’	1.05, d (6.5)	20.1, CH₃	19.2, 31.8, 59.1
8’	1.05, d (6.5)	19.2, CH₃	20.1, 31.8, 59.1
1A	5.17, d (7.0)	97.6, CH
2A	1.74 – 1.88 (m, 2H) 2.37 – 2.58 (m, 3H)	38.2, CH₂
2A	1.74 – 1.88 (m, 2H) 2.37 – 2.58 (m, 3H)	38.2, CH₂
3A	3.77 (bs, 5H)	81.0, CH
4A	3.03 – 3.13 (m, 2H)	76.5, CH	18.8
5A	3.47 – 3.53 (m, 1H)	73.4, CH
6A	1.26 – 1.44 (m, 5H)	18.8, CH₃	73.4, 76.5
1B	4.65 – 4.75 (m, 2H)	100.2, CH
2B	1.52 – 1.65 (m, 3H) 2.17 – 2.24 (m, 1H)	40.9, CH₂
3B	3.60 (bs, 5H)	72.2, CH
4B	2.97, t (9.3)	78.3, CH	18.3, 72.2, 73.8
5B	3.34 – 3.42 (m, 2H)	73.8, CH
6B	1.26 – 1.44 (m, 5H)	18.3, CH₃	73.8, 78.3
1C	5.06 (bs, 1H)	102.2, CH
2C	1.52 – 1.65 (m, 3H) 2.58 – 2.67 (m, 1H)	38.4, CH₂
3C	3.77 (bs, 5H)	81.2, CH
4C	3.03 – 3.13 (m, 2H)	76.7, CH	18.8, 73.6
5C	3.34 – 3.42 (m, 2H)	73.6, CH
6C	1.26 – 1.44 (m, 5H)	18.8, CH₃
1D	4.65 – 4.75 (m, 2H)	100.2, CH
2D	1.74 – 1.88 (m, 2H) 1.95 – 2.02 (m, 1H)	33.3, CH₂
3D	3.85 – 3.93 (m, 1H)	77.5, CH
4D	3.68 – 3.73 (bs, 2H)	70.6, CH
5D	3.60 (bs, 5H)	72.2, CH
6D	1.26 – 1.44 (m, 5H)	17.3, CH₃	70.6
1E	4.99, d (9.0)	99.1, CH
2E	1.52 – 1.65 (m, 3H) 1.92, d (13.0)	45.4, CH₂	99.1
2E	1.52 – 1.65 (m, 3H) 1.92, d (13.0)	45.4, CH₂	71.9, 78.1
3E		71.9, C
3E-CH₃	1.25, s	27.4, CH₃	45.4, 78.1, 99.1
4E	2.93, d (9.5)	78.1, CH	18.9, 72.0
5E	3.68 – 3.73 (bs, 2H)	72.0, CH
6E	1.26 – 1.44 (m, 5H)	18.9, CH	72.0, 78.1