Photocleavable initiator nucleotide substrates for an aldolase ribozyme

Article abstract of DOI:10.1021/jo800639p

(Chemical Equation Presented) We have previously reported the in vitro selection of a ribozyme that catalyzes an aldol reaction between a levulinic amide aldol donor and a benzaldehyde substrate. The selection scheme involved the priming of the RNA librar

Full text of DOI:10.1021/jo800639p

Photocleavable Initiator Nucleotide Substrates for an
Aldolase Ribozyme
Stefan Fusz, Seergazhi G. Srivatsan, Damian Ackermann, and Michael Famulok*
LIMES Institute, Program Unit Chemical Biology and Medicinal Chemistry, c/o Kekulé Institut für
Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Supporting Information
Contents
Compound 1 – 1H-, 13C-, and 31P-NMR spectra………………………………………………....S2-4
Compound 2 – 1H-, and 13C-NMR spectra……………………………………………………....S5-6
Compound 4 – 1H-, and 13C-NMR spectra………………………………………………………S7-8
Compound 6 – 1H-NMR spectrum………………………………………………………………S9
Compound 8 – 1H-, and 13C-NMR spectra…………………………………………………...….S10-11
Compound 10 – 1H-, and 13C-NMR spectra……………………………………………..………S12-13
Compound 11 – 1H-, and 31P-NMR spectra ……………………………………………... ……..S14-15
Compound 15 – 1H-, and 13C-NMR spectra ……………………………………………………..S16-17
S1

S2

S3

S4

S5

S6

S7

S8

S9

S10

S11

O
O
1H-NMR compound 10
O
N
O
N
H
H
OH
3
N
H
NO2
O
8.2
8.0
7.8
(ppm)
7.6
7.4
1.50
(ppm)
2.8
2.7
(ppm)
2.6
5.3
3.70
3.60
3.50
(ppm)
(ppm)
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
(ppm)
4.5
4.0
3.5
3.0
2.5
2.0
1.5
S12

O
O
13C-NMR compound 10
O
N
O
N
H
H
OH
3
N
H
NO2
O
210
200
190
180
170
160
150
140
130
120
(ppm)
110
100
90
80
70
60
50
40
30
20
S13

O
O
1H-NMR compound 11
O
N
O
N
H
H
O
NiPr2
N
3
P
H
NO2 CH3
O
OCH2CH2CN
3.6
3.2
2.8
2.4
1.4
1.2
(ppm)
1.0
0.8
8.2
8.0
7.8
7.6
7.4
7.2
7.0
5.5
(ppm)
(ppm)
5.4
(ppm)
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
(ppm)
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
S14

O
O
31P-NMR compound 11
O
N
O
N
H
H
O
NiPr2
N
3
P
H
NO2 CH3
O
OCH2CH2CN
150
140
130
120
110
100
90
80
(ppm)
70
60
50
40
30
20
10
S15

S16

S
13C-NMR compound 15
H
N
HN
NH2
O
N
H
O
O
3
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
(ppm)
S17