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2D NMR Course Final Problem 2013
NH
HN
O
O
O
OHOH
HH
HH
H
H H
Chemical Formula: C29H38N2O5Exact Mass: 494.2781
Butremycin Butremycin was isolated from a bacterium isolated from a Ghana mangrove. You have been provided with a processed MNova file as well as a pdf containing expansions of all the spectra. Using this data:
1.) Assign all the 1H NMR data and show this on the structure 2.) Assign all 13C NMR data and show this on a structure 3.) Indicate all the COSY data on a structure 4.) Indicate all the HMBC data on a structure 5.) Use the ROESY data to confirm that the stereochemistry is as shown.
Your report should contain:
1.) Annotated spectra 2.) A data table showing your assignments 3.) 4 structures showing
a. 1H assignments (letters on the table or shifts) b. 13C assignments (letters on the table or shifts) c. COSY correlations using arrows d. HMBC correlations using arrows
4.) Analysis of the ROESY data with conformational drawings of relevant sections of the molecule showing the through space correlations
Atom # δ 13C (ppm) 13C mult δ 1H (ppm) mult (Hz)
1H-1H COSY HMBC
A B C D E F G H I J K L M N O P Q R S T U V W X Y Z
Atom # δ 13C (ppm) 13C mult δ 1H (ppm) mult (Hz)
1H-1H COSY HMBC
Ao Bo Co Do Eo Fo Go Ho Io Jo Ko Lo Mo No Oo Po Qo Ro So To Uo Vo Wo Xo Yo Zo
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
-40
-30
-20
-10
0
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220KKMa3x100_SF3_WBH50Min_MDe_1H_for_2DKKMa3x100_SF3_WBH50Min_MDe
5.65.75.85.96.06.16.26.36.46.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.5f1 (ppm)
-40
-30
-20
-10
0
10
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220KKMa3x100_SF3_WBH50Min_MDe_1H_for_2DKKMa3x100_SF3_WBH50Min_MDe
1.06
1.02
1.02
1.06
1.00
0.89
1.77
5.62
5.63
5.64
5.75
5.75
5.77
5.77
5.82
5.84
6.00
6.01
6.02
6.03
6.04
6.04
6.45
6.47
6.48
6.49
7.29
7.32
8.43
0.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.23.33.43.53.63.73.83.94.0f1 (ppm)
-40
-30
-20
-10
0
10
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220KKMa3x100_SF3_WBH50Min_MDe_1H_for_2DKKMa3x100_SF3_WBH50Min_MDe
1.65
7.44
3.84
5.08
15.0
2
7.13
3.72
0.71
5.12
4.02
1.31
1.32
1.14
1.30
1.00
1.11
0.59
0.78
0.78
0.79
0.79
0.81
0.82
0.86
0.87
0.88
1.19
1.19
1.19
1.20
1.21
1.21
1.22
1.22
1.23
1.23
1.23
1.23
1.24
1.24
1.29
1.30
1.80
3.22
3.25
3.55
3.70
3.70
-100102030405060708090100110120130140150160170180190200f1 (ppm)
-500
0
500
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3500
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4500
5000
5500
6000
6500
7000
7500KKMa3x100_SF3_WBH50Min_MDe_13CLMP01308_presat_DMSO_d6_11June13
13.6
718
.08
22.6
725
.94
30.7
832
.08
34.3
237
.91
38.1
239
.68
43.2
343
.44
48.5
148
.54
48.5
748
.57
48.5
848
.63
48.6
648
.66
48.6
748
.67
48.6
848
.69
48.6
948
.71
48.7
348
.75
48.8
048
.84
48.8
448
.86
48.8
848
.90
48.9
148
.93
48.9
348
.94
48.9
448
.95
48.9
648
.96
48.9
748
.97
48.9
849
.00
49.0
249
.04
49.0
549
.06
49.0
749
.08
49.0
849
.09
49.1
049
.10
49.1
149
.12
49.1
349
.14
49.2
449
.28
49.2
849
.40
49.4
249
.43
49.5
749
.62
50.2
950
.44
68.3
672
.50
124.
7712
9.58
130.
4013
1.96
141.
7614
7.78
168.
8817
0.42
195.
54
100105110115120125130135140145150155160165170175180185190195f1 (ppm)
-500
0
500
1000
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2000
2500
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3500
4000
4500
5000
5500
6000
6500
7000
7500
102.
77
124.
77
129.
5813
0.40
131.
96
141.
76
147.
78
168.
8817
0.42
179.
97
184.
72
195.
54
12141618202224262830323436384042444648505254565860626466687072f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6500
7000
7500
13.6
7
18.0
8
22.6
7
23.7
3
25.9
4
30.1
830
.78
32.0
832
.25
33.0
734
.32
37.9
138
.12
39.6
8
43.2
343
.44
48.5
148
.57
48.5
748
.58
48.6
948
.69
48.7
148
.73
48.8
448
.84
48.8
648
.88
48.9
048
.94
48.9
448
.96
48.9
748
.97
48.9
849
.00
49.0
249
.05
49.1
049
.11
49.1
249
.13
49.1
449
.28
49.2
849
.42
49.4
3
68.3
6
72.5
0
48.048.148.248.348.448.548.648.748.848.949.049.149.249.349.449.549.649.749.849.950.050.150.250.350.450.550.650.750.850.951.0f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6500
7000
7500
48.5
148
.57
48.5
748
.58
48.6
948
.69
48.7
148
.73
48.7
548
.80
48.8
448
.84
48.8
648
.88
48.9
048
.94
48.9
448
.95
48.9
648
.97
48.9
748
.98
49.0
049
.02
49.0
449
.05
49.1
049
.10
49.1
149
.12
49.1
349
.14
49.2
449
.28
49.2
8
49.4
049
.42
49.4
3
49.5
7
49.6
2
50.2
9
50.4
4
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f2 (ppm)
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HSQCKKMa3x100_SF3_WBH50Min_MDe
5.65.75.85.96.06.16.26.36.46.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.5f2 (ppm)
125
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170
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HSQCKKMa3x100_SF3_WBH50Min_MDe
0.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.23.33.43.53.63.73.83.9f2 (ppm)
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HSQCKKMa3x100_SF3_WBH50Min_MDe
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
0.5
1.0
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3.0
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7.5
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_COSYKKMa3x100_SF3_WBH50Min_MDe
5.55.65.75.85.96.06.16.26.36.46.56.66.76.86.97.07.17.27.37.4f2 (ppm)
5.4
5.5
5.6
5.7
5.8
5.9
6.0
6.1
6.2
6.3
6.4
6.5
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6.7
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6.9
7.0
7.1
7.2
7.3
7.4
7.5
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_COSYKKMa3x100_SF3_WBH50Min_MDe
5.405.455.505.555.605.655.705.755.805.855.905.956.006.056.106.156.206.256.306.356.406.456.506.556.60f2 (ppm)
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
3.0
3.2
3.4
3.6
3.8
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_COSYKKMa3x100_SF3_WBH50Min_MDe
0.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.4f2 (ppm)
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_COSYKKMa3x100_SF3_WBH50Min_MDe
0.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.8f2 (ppm)
0.6
0.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_COSYKKMa3x100_SF3_WBH50Min_MDe
0.51.01.52.02.53.03.54.04.55.05.56.06.57.0f2 (ppm)
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
3.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.4f2 (ppm)
120
130
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150
160
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
0.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.9f2 (ppm)
125
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)
10
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
2.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.4f2 (ppm)
30
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f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
0.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.23.33.43.53.63.73.8f2 (ppm)
48
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72
74
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
0.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.8f2 (ppm)
14
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44
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_HMBCKKMa3x100_SF3_WBH50Min_MDe
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f2 (ppm)
1
2
3
4
5
6
7
8
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_ROESY_300msKKMa3x100_SF3_WBH50Min_MDe
5.55.65.75.85.96.06.16.26.36.46.56.66.76.86.97.07.17.27.37.47.57.67.7f2 (ppm)
5.6
5.8
6.0
6.2
6.4
6.6
6.8
7.0
7.2
7.4
7.6
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_ROESY_300msKKMa3x100_SF3_WBH50Min_MDe
5.45.55.65.75.85.96.06.16.26.36.46.56.66.76.86.97.07.17.27.37.4f2 (ppm)
0.9
1.0
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
2.0
2.1
2.2
2.3
2.4
2.5
2.6
2.7
2.8
2.9
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_ROESY_300msKKMa3x100_SF3_WBH50Min_MDe
0.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.8f2 (ppm)
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
f1 (
ppm
)
KKMa3x100_SF3_WBH50Min_MDe_ROESY_300msKKMa3x100_SF3_WBH50Min_MDe
