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Table 1. Comparison of 1H NMR for Spinosyn A Pseudoaglycon (28)

Signal

Evans and Black

Paquette et al.

This study

Natural*

H13

6.77 (s, 1H)

6.76 (s, 1H)

6.78 (br s, 1 H)

6.78 (br s, 1 H)

H6

5.88 (d, J = 9.7, 1 H)

5.87 (d, J = 9.7, 1 H)

5.88 (d, J = 9.8, 1 H)

5.88 (d, J = 9.6, 1 H)

H5

5.79 (dt, J = 9.7, 2.7, 1 H)

5.80 (dd, J = 9.7, 2.7, 1 H)

5.80 (dt, J = 9.8, 2.8, 1H)

5.80 (dt, J = 9.8, 2.9, 1H)

H1'

4.85 (d, J = 1.6, 1 H)

4.84 (d, J = 1.2, 1 H)

4.85 (d, J = 1.6, 1 H)

4.85 (d, J = 1.8, 1 H)

H21

4.69 (m, 1 H)

4.70 (m, 1 H)

4.73–4.68 (m, 1 H)

4.73–4.68 (m, 1 H)

H9

4.31 (m, 1 H)

4.29 (m, 1 H)

4.32 (app q, 6.7, 1 H)

4.32 (app q, 6.6, 1 H)

H17

3.69 (m, 1 H)

3.67 (m, 1 H)

3.71–3.66 (m, 1 H)

3.69 (m, 1 H)

H2'

3.56 (m, 1 H)

3.56 (m, 1 H)

3.57–3.53 (m, 1 H)

3.55 (m, 1 H)

–OCH3

3.55 (s, 3 H)

3.54 (s, 3 H)

3.56 (s, 3 H)

3.56 (s, 3 H)

–OCH3

3.50 (s, 3 H)

3.49 (s, 3 H)

3.50 (s, 3 H)

3.50 (s, 3 H)

–OCH3

3.49 (s, 3 H)

3.48 (s, 3 H)

3.50 (s, 3 H)

3.50 (s, 3 H)

H4

3.48 (m, 1 H)

3.47 (m, 1 H)

3.51–3.44 (m, 1 H)

3.51–3.44 (m, 1 H)

H5'

3.48 (m, 1 H)

3.47 (m, 1 H)

3.51–3.44 (m, 1 H)

3.51–3.44 (m, 1 H)

OH

3.48 (m, 1 H)

3.47 (m, 1 H)

Not observed

Not observed

H3'

3.45 (dd, J = 9.4, 3.3, 1H)

3.45 (dd, J = 9.9, 3.3, 1 H)

3.46 (dd, J = 9.4, 3.3, 1 H)

3.47 (dd, J = 9.4, 3.3, 1 H)

H16

3.21 (m, 1 H)

3.21 (m, 1 H)

3.21 (dq, J = 8.8, 6.7, 1 H)

3.21 (dq, J = 9.2, 6.8, 1 H)

H2a

3.12 (m, 1 H)

3.11 (m, 1 H)

3.13 (dd, J = 13.6, 5.1, 1 H)

3.13 (m, 1 H)

H4'

3.12 (m, 1 H)

3.11 (m, 1 H)

3.12 (app t, J = 9.5, 1 H)

3.12 (app t, J = 9.2, 1 H)

H3

3.02 (m, 1 H)

3.00 (m, 1 H)

3.02 (m, 1 H)

3.02 (m, 1 H)

H12

2.87 (m, 1 H)

2.86 (m, 1 H)

2.87 (ddt, J = 11.4, 5.2, 2.6, 1 H)

2.88 (ddt, J = 11.5, 5.2, 2.7, 1 H)

H2b

2.41 (dd, J = 13.4, 7.0, 1 H)

2.39 (dd, J = 13.5, 3.1, 1 H)

2.42 (dd, J = 13.6, 3.3, 1 H)

2.42 (dd, J = 13.6, 3.5, 1 H)

H10a

2.28 (dt, J = 12.8, 7.1, 1 H)

2.26 (m, 1 H)

2.28 (m, 1 H)

2.28 (m, 1 H)

H7

2.16 (m, 1 H)

2.16 (m, 1 H)

2.17 (m, 1 H)

2.17 (m, 1 H)

H8a

1.92 (dd, J = 13.4, 7.0, 1 H)

1.91 (dd, J = 13.2, 7.0, 1 H)

1.93 (dd, J = 13.5, 7.2, 1 H)

1.93 (dd, J = 13.6, 7.3, 1 H)
 

1.67–1.28 (m, 9 H)

1.70–1.22 (m, 10 H)

1.72–1.24 (m, 10 H)

1.71–1.26 (m, 10 H)

H6'

1.28 (d, J = 6.3, 3 H)

1.26 (d, J = 6.2, 3 H)

1.28 (d, J = 6.4, 3 H)

1.28 (d, J = 6.2, 3 H)

Me-16

1.21 (d, J = 6.8, 3 H)

1.20 (d, 3 H, no J value)

1.22 (d, J = 6.8, 3 H)

1.22 (d, J = 6.7, 3 H)

H11

0.93 (m, 1 H)

0.91 (m, 1 H)

0.92 (dq, J = 11.7, 6.7, 1 H)

0.92 (dq, J = 11.7, 6.6, 1 H)

H23

0.82 (t, J = 7.5, 3 H)

0.81 (t, J = 7.5, 3 H)

0.82 (t, J = 7.5, 3 H)

0.82 (t, J = 7.5, 3 H)

*1H NMR data for natural 28 were obtained by using a sample of natural spinosyn A pseudoaglycone kindly provided by L. A. Paquette.

1. Evans, D. A. & Black, W. C. (1993) J. Am. Chem. Soc. 115, 4497.

2. Paquette, L. A., Collado, I. & Purdie, M. (1998) J. Am. Chem. Soc. 120, 2553.