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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
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).