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PYA 11057
Product Information Molecular Structure

6-Aza-2'-deoxyuridine

Notes: 6-Aza-2'-deoxyuridine (6-aza-dU) has a nitrogen atom in place of the methine group at position 6 of the uracil ring.

Description: The nitrogen atom in place of the methine group at position 6 of the uracil ring in 6-Aza-2'-deoxyuridine (6-aza-dU)1 results in a significant lowering of the pKa of the N3 hydrogen (6.8) vs. that of 2'-deoxyuridine (9.3).2 Unlike dU, 6-aza-dU is deprotonated at neutral pH, thus bestowing the uracil base with a negative charge. Further, there are significant conformational changes imparted by the presence of the 6-aza substitution: 6-Aza-dU has a high-anti conformation and is present in solution with N-type sugar pucker.2

See also 6-Aza-dU CEP, the phosphoramidite version for incorporation of 6-aza-dU residues into oligonucleotides, the nucleoside 6-Azathymidine, and its phosphoramidite 6-Azathymidine CEP.

(1) (a) Kara, J.; Sorm, F. Coll. Czech. Chem. Commun. 1963, 28, 1441-1448. (b) Holy, A.; Cech, D. Coll. Czech. Chem. Commun. 1974, 39, 3157-3167. Drasar, P.; Hein, L.; Beranek, J. Coll. Czech. Chem. Commun. 1976, 41, 2110-2123. (d) Freskos, J. N. Nucleosides Nucleotides 1989, 8, 549-555.

(2) Seela, F.; Chittepu, P. J. Org. Chem. 2007, 72, 4358-4366.

6-Aza-2'-deoxyuridine
Product Details Product Pricing

MF: C8H11N3O5

MW: 229.20

CAS NO: 20500-29-2

Storage Conditions: 5 oC

Purity≥95%

Availability: 

Stock maintained. Ships within 1-3 days.

Unit Weight Unit Price Quantity
50 mg $110.00
100 mg $175.00
 
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