Bertin et al. 10.1073/pnas.0707198104.

Supporting Information

Files in this Data Supplement:

SI Table 1
SI Figure 6
SI Figure 7
SI Table 2
SI Table 3




SI Figure 6

Fig. 6. Structure of m-tyrosine (3′-hydroxyphenylalanine) with atom numbering and corresponding o- and p-hydroquinones (3′,4′-dihydroxyphenylalanine and 2′,5′-dihydroxyphenylalanine, respectively) representing likely products of additional hydroxylation.





SI Figure 7

Fig. 7. Comparison of the phytotoxicity of the three root exudate fractions on lettuce seedlings.





Table 1. Inhibition of radicle elongation of selected plant species by m-tyrosine

 

IC50,µM

Cress

23

Mouse-ear chickweed

9

Birdsfoot trefoil

42

Annual bluegrass

47

Broadleaf plantain

72

Black medic

84

IC50 represents the concentration of m-tyrosine required to observe 50% inhibition.





Table 2. NMR-spectroscopic data of isolated m-tyrosine (600 MHz for 1H, 126 MHz for 13C, solvent 2H2O)

Carbon no.

d

, ppm

Proton no.

d

, ppm

J, Hz

NOESY correlations

HMBC correlations

C-1

174.1

     

C-2

56.0

2-H

3.99

J3

a,2 = 8.4, J3b,2 = 4.3		 

C-1, C-3, C-1′

C-3

36.4

3-H

a

3.08

J3

a,3b = 14.7

2′-H, 6′-H

C-1, C-2, C-1′, C-2′, C-6′

  

3-H

b

3.25

 

2′-H, 6′-H

C-1, C-2, C-1′, C-2′, C-6′

C-1′

137.2

  

J4,5

= 2		 

1"

C-2′

116.2

2′-H

6.83

J2′,4′

= 1.5, J2′,6′ = 1

3-H

a, 3-Hb

C-3, C-4′, C-6′

C-3′

156.1

     

C-4′

114.7

4′-H

6.87

J4′,5′

= 8.4		 

C-2′, C-6′

C-5′

130.7

5′-H

7.31

J5′,6′

= 7.8		 

C-3′, C-1′

C-6′

121.6

6′-H

6.89

 

3-H

a, 3-Hb

C-3, C-2′, C-4′

HMBC, heteronuclear multiple bond correlation.

 





Table 3. Gradient used for the separation of the AccQ tag amino acid derivatives by HPLC

 

Time

% Eluent A

% Eluent B

1

0.01

100

0

2

0.5

97

3

3

12

95

5

4

15

92

8

5

45

65

35

6

49

65

35

7

50

0

100

8

60

0

100

9

61

100

0

10

68

100

0