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Volumn , Issue 7, 2008, Pages 1066-1070

First route to phosphoramidites of N2-hydrazinoaryl- and N 2-azoaryl-dG adducts and their site-selective incorporation into DNA oligonucleotides

(3) Böge, Nicolas a Schröder, Marcus a Meier, Chris a

a UNIVERSITY OF HAMBURG (Germany)

Author keywords

Aromatic amines; Chemical carcinogenesis; Cross coupling; DNA damage; N2 adducts

Indexed keywords

CARCINOGEN; DNA; DNA HYBRID; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID;

ARTICLE; BREAST CANCER; DNA SYNTHESIS; STRUCTURE ACTIVITY RELATION; TEMPERATURE; THERMOSTABILITY; ULTRAVIOLET RADIATION;

EID: 43049178005 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072659 Document Type: Article

Times cited : (2)

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- 4 and the solvent was removed in vacuo. The product was isolated by column chromatography using PE-EtOAc (10% → 35%).
- 4 and the solvent was removed in vacuo. The product was isolated by column chromatography using PE-EtOAc (10% → 35%).

34
- 43049157751
- Compound 7a: The general procedure was conducted with 3.05 g of 5 (4.40 mmol) and 1 mL of 6a (8.8 mmol, yield 2.52 g (3.52 mmol, 80, of 7a as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6, δ, 8.46 (s, 2 H, H-8, 7.43-6.82 (m, 9 H, HAr, 6.67 (dd, 3JH,H, 7.3 Hz, 3JH,H, 7.2 Hz, 1 H, H-1′, 5.34 (s, 2 H, NH, 4.42-4.19 (m, 2 H, H-a, 3.72-3.71 (m, 3 H, H4′, H5′a, H5′b, 3.06 (t, 3JH,H, 6.9 Hz, 3JH,H, 6.9 Hz, 2 H, Hb, 2.97-2.91 (m, 1 H, H2′a, 1.91 (s, 1 H, H2′b, 0.75 [s, 9 H, Si(CH3) 3 at C3′, 0.80 [s, 9 H, Si(CH3)3 at C5′, 0.00 [s, 6 H, Si(CH3)2, 0.15 [2 x s, 2 x 3 H, Si(CH3)2] ppm. 13C NMR 101 MHz, DMSO-d6, δ, 1
- +.

35
- 43049159301
- Compound 10a: 1NMR (400 MHz, benzene-d 6, δ= 7.84 [s, 1 H, H-8 (I, 7.81 [s, 1 H, H-8 (II, 7.71-7.41 [m, 44 H, HAr (I, II, DMTr-H (I, II, 6.25 [dd, 3JH,H, 6.4 Hz, 3JH,H, 6.3 Hz, 2 H, H-1′ (I, II, 4.74-4.58 [m, 2 H, NH (I, 4.47-4.37 [m, 2 H, NH (H, 4.16-4.05 [m, 4 H, H-a (I, II, 3.58-3.35 (m, 12 H, OCH 3, H-5′a/b (I, II, H-b(I, 3.15-3.02 [m, 2 H, H-b (II, 2.54-2.29 (m, 12 H, i-PrH (I, II, H-α (I, II, H-2′a/b (I, II, 1.81 [t, 2 H, H-β (I, 1.73 [m, 2 H, H-β(II, 1.15-1.01 [m, 24 H, CH3i-Pr (I, II, ppm. 13C NMR 101 MHz, benzene-d6, δ= 160.1, 159.3, 158.7, 148.2, 145.8, 143.3, 138.0, 137.4, 136.1, 132.0, 131.4, 130.6, 130.1, 129.8, 119.0, 113.7, 113.0, 111.0, 87.1, 74.4, 74.2, 66.0, 54.8, 45.3, 43.6, 35,1, 24.7, 24.6, 22.8 ppm. 31
- -1. MS-FAB: m/z

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