Supporting Information for Amphiphilic Siderophore Production by Oil

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Page 1 ... 450. 500. 550. 600. 650. 700. 750. 800. 850. 900. 950 m/z. 0. 100. %. BUT083010MH1 44 (0.849) Cm (26:45). TOF MSMS 858.00ES+. 219. 450.24.
Electronic Supplementary Material (ESI) for Metallomics. This journal is © The Royal Society of Chemistry 2014

Supporting Information for Amphiphilic Siderophore Production by Oilassociating Microbes Michelle P. Kem, Hannah K. Zane, Stephen D. Springer, Julia M. Gauglitz, and Alison Butler* Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA 93106-9510

Table S1. The m/z values for the ‘b’ ions of isolated amphibactin siderophores from ESI-MS/MS analysis. Alcanivorax borkumensis SK2

Vibrio sp. S2A

Vibrio sp. S1B

‘b’

E

H

I

‘b’

D

E

H

I

‘b’

S

D

E

H

b3

668

670

696

b3

642

668

670

696

b3

640

642

668

670

b2

581

583

609

b2

555

581

583

609

b2

553

555

581

583

b1

409

411

437

b1

383

409

411

437

b1

381

383

409

411

Figure S1. The tandem mass spectra of amphibactins E and amphibactin I isolated from Alcanivorax borkumensis SK2.The ESIMS/MS of amphibactin H is shown in Figure 2. y3

alcan nsw 82010 peak 6 msms 858 BUT083010MH1 44 (0.849) Cm (26:45) 100

y3

alcan nsw 82010 peak 8 msms 886 TOF MSMS 858.00ES+ BUT083010MJ1 29 (0.554) Cm (13:29) 219 100

450.24

TOF MSMS 886.00ES+ 471

450.24

[M+H] + 886.59

Amphibactin I (C18:1)

[M+H] +

Amphibactin E (C16:1)

858.54

%

%

b1 409.33 451.25

b2

y2 278.14 260.13

0 50

100

150

200

250

300

452.24

400

y2

450

500

550

600

451.25

b2

840.52

395.35

861.54

260.13

696.50

700

750

800

850

900

m/z 950

697.49

868.58

888.60

610.46

377.34 452.24

279.16

862.58

650

437.35

609.45 860.56

669.44

582.41

b3

b1

278.15

b3 668.47

581.42

367.31

350

887.57

859.56

698.51

889.60

611.47

0

m/z 100

200

300

400

500

600

700

800

900

1000

Figure S2. The tandem mass spectra of amphibactins D, E, H and I isolated from Vibrio sp. S2A. S2A peak B msms BUT072210MA3 45 (0.869) Cm (43:57) 100

s2a 80% peak4 msms 860

y3 450.27 450.29

[M+H] +

b1 383.33 451.28

341.31

260.16

b3 642.47

b2 555.40

833.58

643.45

833.62

814.54

0

m/z 150

200

250

300

350

400

S2A peak C msms 858

450

500

550

600

650

700

100

800

b1 y2 411.37 278.16 369.35 451.26 260.14 351.33

b3 670.50

b2 583.46

[M+H] + 860.63

671.49

842.62

m/z 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900

y3 450.27

TOF MSMS 858.00ES+ BUT072210MB1 57 (1.094) Cm (54:64) 135 100

TOF MSMS 886.00ES+ 44 +

[M+H]

886.63 886.61 886.68

450.25

Amphibactin E (C16:1)

Amphibactin I (C18:1)

[M+H] +

b1 409.35 367.34

451.28

b2 581.46

b3 668.49 668.52 669.50

%

%

858.59

y2 278.16 260.15

859.59

y2 278.16

840.61

0

887.64

b1 437.39 395.38

b3 696.54

b2 609.49 451.28

260.14

m/z 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900

861.62

0

850

S2A peak d2 msms 886

y3 450.27

BUT072210MA6 63 (1.210) Cm (41:67)

750

TOF MSMS 860.00ES+ 335

Amphibactin H (C16:0)

832.57

%

%

Amphibactin D (C14:0)

y2 278.16

y3 450.26

TOF MSMS 832.00ES+ BUT080310MB1 47 (0.903) Cm (44:58) 95 100

697.54

610.49

886.57 868.64

0

m/z 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900

Figure S3. The tandem mass spectra of amphibactins D, E, H and I isolated from Vibrio sp. S1B. y3

[M+H]+

y3 [M+H]+

Amphibactin E (C16:1)

Amphibactin S (C14:1)

y2

b2

b1

b3 y2

y3

b1

b1

b2

b3

[M+H]+

y3

[M+H]+

Amphibactin H (C16:0)

Amphibactin D (C14:0)

y2

b2

b3

y2

b1

b2

b3