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Table 1 LC-HRMS analysis of SPE-treated supernatants of bacterial cultures expressing a CDPS/CDO couple originating from the same operon

From: In vivo characterization of the activities of novel cyclodipeptide oxidases: new tools for increasing chemical diversity of bioproduced 2,5-diketopiperazines in Escherichia coli

Host of origin

Searched compound

Name

Molecular formula of [M + H]+

Expected m/z

Observed m/z

RT (min)a

Peak area (EIC)

Nocardiopsis potens

cFA

C12H15N20+2

219.1128

219.1127

32.75

8.33E+05

∆cFA

C12H13N20+2

217.0972

217.0971

33.57

3.49E+04

   

217.0971

38.58

3.04E+05

∆∆cFA

C12H11N20+7

215.0815

–

–

–

cFY

C18H19N20+3

311.1390

311.1390

37.41

4.43E+05

∆cFY

C18H17N20+3

309.1234

309.1234

38.75

3.34E+05

   

309.1234

39.57

4.58E+05

∆∆cFY

C18H15N20+3

307.1077

307.1077

44.02

6.13E+04

cFM

C14H19N202S+

279.1162

279.1162

39.11

3.92E+06

∆cFM

C14H17N202S+

277.1005

277.1006

40.08

7.76E+05

   

277.1006

42.16

7.75E+05

∆∆cFM

C14H15N202S+

275.0849

275.0849

43.17

3.86E+04

   

275.0849

44.05

1.59E+05

cFL

C15H21N20+2

261.1598

261.1598

40.93

1.36E+05

∆cFL

C15H19N20+2

259.1441

259.1441

41.36

2.17E+05

   

259.1441

44.26

5.70E+05

∆∆cFL

C15H17N20+2

257.1285

257.1284

44.79

1.59E+04

   

257.1284

45.75

9.23E+04

cFF

C18H19N20+2

295.1441

295.1441

41.81

6.13E+06

∆cFF

C18H17N20+2

293.1285

293.1285

42.58

4.09E+05

   

293.1284

43.17

7.77E+06

∆∆cFF

C18H15N20+2

291.1128

291.1128

46.98

1.62E+05

   

291.1128

47.9

2.55E+05

Actinomadura oligospora (pathway 1)

cFY

C18H19N20+3

311.1390

311.1390

37.62

1.01E+07

∆cFY

C18H17N20+3

309.1234

309.1233

37.17

1.37E+05

   

309.1234

38.67

4.09E+06

   

309.1233

39.78

2.26E+06

   

309.1233

40.14

2.00E+05

∆∆cFY

C18H15N20+3

307.1077

307.1077

43.6

8.98E+04

   

307.1078

44.49

4.63E+05

cYY

C18H19N20+4

327.1339

327.1339

29.92

1.25E+05

∆cYY

C18H17N20+4

325.1183

325.1183

32.60

2.21E+05

∆∆cYY

C18H15N20+4

323.1026

323.1028

41.48

5.52E+04

cWY

C20H20N30+3

350.1499

350.1499

37.65

4.37E+05

∆cWY

C20H18N30+3

348.1343

–

–

–

∆∆cWY

C20H16N30+3

346.1186

–

–

–

Streptomyces catenulae

cFY

C18H19N20+3

311.1390

311.1390

37.51

9.80E+06

∆cFY

C18H17N20+3

309.1234

309.1233

37.18

9.64E+04

   

309.1234

38.76

1.89E+06

   

309.1234

39.59

3.13E+06

   

309.1234

39.97

1.81E+05

∆∆cFY

C18H15N20+3

307.1077

307.1077

42.82

1.74E+04

   

307.1076

43.64

5.59E+04

cWY

C20H20N30+3

350.1499

350.1499

37.66

3.41E+05

∆cWY

C20H18N30+3

348.1343

–

–

–

∆∆cWY

C20H16N30+3

346.1186

–

–

–

Streptomyces rimosus

cWY

C20H20N30+3

350.1499

350.1498

37.40

1.01E+07

∆cWY

C20H18N30+3

348.1343

348.1343

38.41

1.81E+06

   

348.1340

38.73

9.73E+06

   

348.1342

39.02

2.45E+06

∆∆cWYb

C20H16N30+3

346.1186

–

–

–

cWW

C22H21N40+2

373.1659

373.1659

41.62

2.71E+06

∆cWWb

C22H19N40+2

371.1503

–

–

–

∆∆cWW

C22H17N40+2

369.1346

–

–

–

Streptomyces sp. NRRL F–5123

cWP

C16H18N30+2

284.1394

284.1393

38.08

1.80E+05

∆cWP

C16H16N30+2

282.1237

282.1235

37.33

1.80E+07

∆cWP

C16H14N30+2

280.1081

280.1081

37.36

1.04E+05

cWL

C17H22N30+2

300.1707

300.1706

39.8

1.19E+06

∆cWL

C17H20N30+2

298.1550

298.1550

40.64

7.38E+05

∆∆cWL

C17H18N30+2

296.1394

–

–

–

Actinomadura oligospora (pathway 2)

cWW

C22H21N40+2

373.1659

373.1658

41.04

1.28E+07

∆cWW

C22H19N40+2

371.1503

371.1504

41.18

1.50E+05

∆∆cWW

C22H17N40+2

369.1346

369.1345

41.15

1.00E+04

Streptomyces aidingensis

cWL

C17H22N30+2

300.1707

300.1706

40.06

3.26E+06

∆cWL

C17H20N30+2

298.1550

298.1550

40.95

1.28E+07

∆∆cWL

C17H18N30+2

296.1394

–

–

–

cFL

C15H21N20+2

261.1598

261.1598

41.18

7.00E+04

∆cFL

C15H19N20+2

259.1441

–

–

–

∆∆cFL

C15H17N20+2

257.1285

–

–

–

cWF

C20H20N30+2

334.1550

334.1550

41.65

1.29E+05

∆cWF

C20H18N30+2

332.1394

332.1393

42.66

1.96E+05

∆∆cWL

C20H16N30+2

330.1237

–

–

–

  1. Experiments from bacterial transformations to LC-HRMS were performed twice independently and each sample was injected twice on an LC-HRMS; one set of results (one experiment, one injection) is presented; differences between samples corresponding to the same experimental condition are indicated
  2. aRT, retention time
  3. bTrace amounts were detected in some analysis