University of Groningen Chemistry-based enzyme detection ... · Thesis Marilena Ourailidou.indb 129...

University of Groningen

Chemistry-based enzyme detection and inhibition in epigeneticsOurailidou, Maria-Eleni

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Citation for published version (APA):Ourailidou, M-E. (2016). Chemistry-based enzyme detection and inhibition in epigenetics. [Groningen]:University of Groningen.

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Thesis Marilena Ourailidou.indb 129 29-08-16 20:11

Chapter 5

Light-controlled HDAC inhibitors

Chapter 5

Figure 1.

Figure 2.

Chapter 5

Figure 3. 1 12

89 10 11 9

10 118 9

4 51 2

1 3 4 5 7

Chapter 5

in vivo

5Figure 4.

Chapter 5

1 2 3 5 6 7 8 12

Chapter 5

Figure 5. 12

Chapter 5

H2 2 H2 JH2 J H2 H3 J

H J H H

H2 2 H2 J H2 JH2 H2 H3 J

H J H H

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H3 H H J HJ H J H

trans-1: trans 1 8

H2 2 H2J H2 J H2

H H H HH

cis-1: cis 1 8

trans-1 cis-1

H2 2 H2 J H2 JH2 J H J H J

H J H J HH H H

H2 2 H2 JH2 J H2 H3 H2J H J H J

Chapter 5

H2 2H2 J H2 J H2 H3

H J HJ H J H H

trans-2: trans 1 8

H2 2 H2 J H2J H2 H J H J

H H H HH

cis-2: cis 1 8

trans-2cis-2

H2 2 H2 J H2 JH2 J H J H

H H H HH

H2 2H2 J H2 J

CH2 H3 J H JH H H J

trans-3: trans- 1 8

H2 2 H2 H2J H2 J H2 J H

J H H JH J H J H H

cis-3: trans- 1 8

trans-3cis-3

H2 2 H2 H2 JH2 J H2 J H

J H H J HJ H H H H

Chapter 5

H2 2 H2H2 H3 J H J

-ate 20

H2 2 H2 JCH2 J H2 H3 H3

J H H J HH

trans-4: trans 1 8 -21

H2 2H2 J H J

CH J H2 H3 J HH J H H

cis-4: cis 1 8 -trans-4

cis-4H2 2 H2 J

H J H J H2H3 J H H

J H H H H

H2 2 H2 JH2 J H2 H3 J

H J H J H JH J H HH

Chapter 5

-te. 22

H2 2 H2 JH2 J H2 H3 H3

J H J H H JH J H J H

trans-5: trans 1 8 -23

H2 2 H2 JH2 J H2 H3 HJ H J H J

H J H J HH H

cis-5: cis 1 8 -trans-5

cis-5H2 2 H2 J H2

J H2 H3 J HH J H H J

H H H H

CH3 H H J HJ H H

H2 HH H H J H

JCH3 H2 H2 JCH2 J H2 J H2

H J H HH H

trans-6: trans 1 7

Chapter 5

H2 H2 J H2J H2 H J H

H H H HH

cis-6: trans- 1 7

trans-6cis-6

H2 H2 J H2 JH2 J H J HH H H H

J J JJ

H2 2 H2 H2 JCH2 J H2 H3 H3

H3 J H J HJ H J H +

trans-7: trans 1

H2 2 H2CH2 J H2 J H2CH3 H3 H3 J H

J H J H J HH H H

cis-7: cis 1 8-trans-7

cis-7H2 2 H2

H2 J H2 J H2CH3 H3 H3 J H

J H J H J HH H H

Chapter 5

5J H2 J

H2 H3 J H JH

29J H2 J

H2 H2 H3 J HJ H

J H2 J H2 H3 JH J H J H J

J H2 JCH2 H3 H3 J HJ H J H J H

trans-8: trans-N -31

JH2 J H2 H3 J

H J H J H JH H H

cis-8: cis-Ntrans-8

cis-8 JH2 J H2 H3 J

H H J H HH

JH2 J H2 H3 H2

J H J H HJ H J H

Chapter 5

trans-9: trans-N -32

JH2 J H2 H2 J

H H J H JH H H

cis-9: trans-N -trans-9

cis-9J H2 J H2 H2

J H J H J HJ H H H

H3H2 J H J H J

H J H H

H2H3 H3 J H J

H J H J H

trans-10: trans N -34

H2 H2 JH J H J H J

cis-10: cis Ntrans-10

cis-10H2 H3 J H

Chapter 5

H2 H3 H2J H H J HJ H

trans-11: trans N -35

H2 H2 J HH J H J H

cis-11: cis Ntrans-11

cis-11H2 H2 J H J

H J H J HH H H

JCH3 J H2 J H J

J H JH J H

J H3 H3 JH2 J H J H

J H J H JH J H

trans-12: trans-N-

H3J H J H J

H J H J H JH H H

cis-12: cis-N- -de. trans-12

cis-12H3 J H H

J H J H HH

Chapter 5

Figure S1. 1-12

Figure S2. 1-12

Chapter 5

Figure S3.

Figure S4 1-12

Chapter 5

Figure S5. 1-12

Figure S6. 1212

t0.5 = 74 min

t0.5 = 4.25h

t0.5 = 67 min

Chapter 5

5Figure S7.

Figure S8.

Chapter 5

Figure S9.

Chapter 5

5Figure S10.

trans-cis

Figure S11.

Chapter 5

Figure S12. 12

5Figure S13.

Chapter 5

In situ

Figure S14. 12 12

Figure S15.

Chapter 5

5Figure S16.

trans-cis

Figure S17. 3 3

Chapter 5

Figure S18.

Figure S19.

Chapter 5

Figure S20.

Figure S21.

Figure S22.

Chapter 5

Figure S23.

Chapter 5

trans and cis-12

Figure S24.12

in vitro via

Chapter 5

University of Groningen Chemistry-based enzyme detection ... · Thesis Marilena Ourailidou.indb 129...

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