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Exploring tryptamine conjugates as pronucleotides of phosphate-modified 7-methylguanine nucleotides targeting cap-

dependent translation
By Golojuch, Sebastian; Kopcial, Michal; Strzelecka, Dominika; Kasprzyk, Renata; Baran, Natalia; Sikorski, Pawel J.;
Kowalska, Joanna; Jemielity, Jacek
From Bioorganic & Medicinal Chemistry, 28(13), 115523; 2020
Published by Elsevier B.V.

Step 1

Products 1H-Purinium, 2-amino-6,9-dihydro-6-oxo-7-(phenylmethyl)-9-β-D-ribofuranosyl-, 71%, CAS

RN: 71171-61-4
Reactants Guanosine, CAS RN: 118-00-3
Benzyl bromide, CAS RN: 100-39-0
Reagents Ammonia, CAS RN: 7664-41-7
Solvents Dimethyl sulfoxide, CAS RN: 67-68-5
Water, CAS RN: 7732-18-5
Acetone, CAS RN: 67-64-1
Procedure
1. Add benzyl bromide (20.1 mL, 169.2 mmol) to guanosine (6.0 g, 21.2 mmol) solution in
DMSO (53 mL).

2. Stir the reaction mixture at room temperature for 3 hours.

3. Add 25% ammonia solution in water dropwise to the mixture till pH value of the reaction
mixture reaches value 7.

4. Add acetone (250 mL) to the mixture continuously additional portions of 25% ammonia
solution in water dropwise to the mixture till pH value of the mixture stabilizes at value
7.

5. Precipitate the crude from the solution.

6. Cool the suspension to 4 °C.

7. Filter the precipitate and wash triply with cold acetone.

8. Dry the mixture overnight over P4O10 in a vacuum to obtain the product.

Scale gram
1H NMR (400 MHz, DMSO-d6) δ 9.43 (s, 1H), 7.49 - 7.45 (m, 2H), 7.42 - 7.33 (m, 3H), 6.98 (s, 2H),
5.83 (d, J = 4.1 Hz, 1H), 5.67 (s, 1H), 5.70 - 5.59 (m, 2H), 5.30 (s, 1H), 5.28 (s, 1H), 4.45
(t, J = 4.6, 4.1 Hz, 1H), 4.13 (t, J = 5.0, 4.6 Hz, 1H), 3.99 (q, J = 5.0, 3.3 Hz, 1H), 3.71 (dd,
J = 12.2, 3.3 Hz, 1H), 3.59 (dd, J = 12.2, 3.3 Hz, 1H)
HRMS ESI (+) calculated m/z for C17H20N5O5+ [M + H]+ 374.14590, found 374.14582
RT 9.0 min
State white solid
CAS Method Number 3-614-CAS-4645439
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