S1

Supporting Information for Synthesis and Photosensitivity of

Isoxazolin-5-one Glycosides

Tobias Becker†, Prashant Kartikeya

‡, Christian Paetz

†, Stephan H. von Reuß

†, Wilhelm Boland

†*

† Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans-Knoell-Straße 8, D-07745 Jena, Germany

‡ Indian Institute of Technology, 721302 Kharagpur, India

*boland@ice.mpg.de

1H NMR and

13C NMR spectrum of comp. 1 in D2O (400 MHz, 100 MHz) ...………..S2

1H NMR and

13C NMR spectrum of comp. 2 in D2O (400 MHz, 100 MHz) ...………..S3

1H NMR and

13C NMR spectrum of comp. 3 in D2O (400 MHz, 100 MHz) ...………..S4

1H NMR and

13C NMR spectrum of comp. 4 in D2O (400 MHz, 100 MHz) ...………..S5

1H NMR and

13C NMR spectrum of comp. 5 in D2O (400 MHz, 100 MHz) ...………..S6

Decay curve of uridine in buffer …………....………………………………………..S7

pH stability plots of compound 1 ….………...………………………………………..S8

Decay curve of comp. 1 in buffer ….………...………………………………………..S8

Decay curve of comp. 2 in buffer …….…….………………………………………..S9

Decay curve of comp. 3 in buffer …….…….………………………………………..S10

Decay curve of comp. 4 in buffer ……….….………………………………………..S11

Decay curve of comp. 5 in buffer …………..………………………………………..S12

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2015

S2

S3

S4

S5

S6

S7

50 100 150 200 250 300 350 400

0.38

0.40

0.42

0.44

Ab

so

rpti

on

(=

260 n

m)

t [s]

Equation y = a + b*x

Weight Instrumental

Residual Sum of Squares

6.2349E-4

Adj. R-Square 0.99969

Value Standard Error

Uridine Intercept 0.41797 6.49704E-5

Uridine Slope -4.42975E-5 2.59811E-7

Fig. S1: Decay curve of uridine in Na2HPO4/NaH2PO4; max = 254 nm; I261 = 0.18 mW/cm2; pH

= 7; dlamp = 5 cm; rt; the error bars show the standard deviation (n = 5).

S8

0 5 10 15 20 25 30

0

25

50

75

100

pH 0

pH 5.1

pH 5.1 beta-

Glucosidase

pH 7.1

pH 8.3

pH 9.4

pH 10.5

pH 11.3

A/A

0 ( =

261 n

m)

[%]

t [min]

Fig. S2: Absorption of compound 1 at 261 nm under different pH conditions over the time.

40 50 60 70 80 90 100 110 120 130

0.30

0.32

0.34

0.36

0.38

0.40

Ab

so

rpti

on

( =

261 n

m)

t [s]

Equation y = a + b*x

Weight Instrumental

Residual Sum of Squares

0.0086

Adj. R-Square 0.99978

Value Standard Error

Glc Intercept 0.41931 4.07212E-4

Glc Slope -8.39131E-4 4.71408E-6

Fig. S3: Decay curve of comp. 1 in Na2HPO4/NaH2PO4; max = 254 nm; I261 = 0.18 mW/cm2; pH

= 7; dlamp = 5 cm; rt; the error bars show the standard deviation (n = 5).

S9

40 50 60 70 80 90 100 110 120 130

0.30

0.32

0.34

0.36

0.38

0.40A

bs

orp

tio

n ( =

26

1 n

m)

t [s]

Equation y = a + b*x

Weight Instrumental

Residual Sum of Squares

0.13264

Adj. R-Square 0.99931

Value Standard Error

Xyl Intercept 0.43016 7.3051E-4

Xyl Slope -8.49912E-4 8.45041E-6

Fig. S4: Decay curve of comp. 2 in Na2HPO4/NaH2PO4; max = 254 nm; I261 = 0.18 mW/cm2; pH

= 7; dlamp = 5 cm; rt; the error bars show the standard deviation (n = 5).

S10

40 50 60 70 80 90 100 110 120 130

0.30

0.32

0.34

0.36

0.38

0.40

Ab

so

rpti

on

( =

26

1 n

m)

t [s]

Equation y = a + b*x

Weight Instrumental

Residual Sum of Squares

0.06264

Adj. R-Square 0.99934

Value Standard Error

Malt Intercept 0.40723 6.59121E-4

Malt Slope -7.63293E-4 7.42702E-6

Fig. S5: Decay curve of comp. 3 in Na2HPO4/NaH2PO4; max = 254 nm; I261 = 0.18 mW/cm2; pH

= 7; dlamp = 5 cm; rt; the error bars show the standard deviation (n = 5).

S11

40 50 60 70 80 90 100 110 120 130

0.30

0.32

0.34

0.36

0.38

0.40A

bs

orp

tio

n ( =

26

1 n

m)

t [s]

Equation y = a + b*x

Weight Instrumental

Residual Sum of Squares

6.13097E-4

Adj. R-Square 0.99986

Value Standard Error

Frc_unp Intercept 0.41902 2.75748E-4

Frc_unp Slope -6.99663E-4 3.11953E-6

Fig. S6: Decay curve of comp. 4 in Na2HPO4/NaH2PO4; max = 254 nm; I261 = 0.18 mW/cm2; pH

= 7; dlamp = 5 cm; rt; the error bars show the standard deviation (n = 5).

S12

40 50 60 70 80 90 100 110 120 130

0.30

0.32

0.34

0.36

0.38

0.40A

bs

orp

tio

n ( =

26

1 n

m)

t [s]

Equation y = a + b*x

Weight Instrumental

Residual Sum of Squares

0.19894

Adj. R-Square 0.99882

Value Standard Error

Frc_pol Intercept 0.40811 6.86016E-4

Frc_pol Slope -6.78695E-4 8.80663E-6

Fig. S7: Decay curve of comp. 5 in Na2HPO4/NaH2PO4; max = 254 nm; I261 = 0.18 mW/cm2; pH

= 7; dlamp = 5 cm; rt; the error bars show the standard deviation (n = 5).