Table 3 Substrate scope of C–H ethylation of the ssDNA oligonucleotidesa

From: Late-stage guanine C8–H alkylation of nucleosides, nucleotides, and oligonucleotides via photo-mediated Minisci reaction

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Entry

Oligonucleotides & sequence

Yield [%]c

Calcd. exact mass

Exptl. m/z (MALDI-FTMS)

1b

dGpT

5′-dGT-3′

70d

599.1741

[M + H]+ = 600.1807e

2b

dTpG

5′-dTG-3′

65d

599.1741

[M + 2Na]+ = 644.1451e

3

ON 9

5′-dGTTCC-3′

43

1481.3129

[M + H]+ = 1482.32446

4

ON 10

5′-dTTCCG-3′

33

1481.3129

[M + H]+ = 1482.32241

5

ON 11

5′-dCGTT-3′

63

1192.2665

[M + H]+ = 1193.27804

6

ON 12

5′-dTTGCC-3′

80

1481.3129

[M + H]+ = 1482.32368

7

ON 13

5′-dCATGT-3′

64

1505.3241

[M + H]+ = 1506.34015

8

ON 14

5′-dCCCGTTT-3′

62

2074.4053

[M + H]+ = 2075.40114

9

ON 15

5′-dCACGTTT-3′

69

2098.4165

[M + H]+ = 2099.43403

10

ON 16

5′-dCCTTGTTCC-3′

51

2667.4977

[M + H]+ = 2668.47158

11

ON 17

5′-dCACTTGTTC-3′

59

2691.5089

[M + H]+ = 2692.49906

  1. aGeneral condition: oligonucleotide (100 nmol), ethylboronic acid (400.0 equiv.), MesAcr (50 mol%), (NH4)2S2O8 (200.0 equiv.), TFA (50.0 equiv.), and catechol (100.0 equiv.) in MeCN (0.25 mL), H2O (0.25 mL), irradiated by 85 W white light at r.t. for 16 h.
  2. bThe reaction was irradiated by 10 W LED and carried out at 0 °C for 5 h. cYields were determined by LC-MS and used the analytical method B. dYields were determined by LC-MS and used the analytical method A. eThe mass data was collected by using HRMS.
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