ChemicalBook CAS DataBase List Pseudouridine

Pseudouridine synthesis

8synthesis methods

Product Name:Pseudouridine
CAS Number:1445-07-4
Molecular formula:C9H12N2O6
Molecular Weight:244.2

β-Pseudouridine is the C-5 glycoside isomer of the nucleoside uridine (Item No. 20300). It is formed when uridine in RNA undergoes site-specific isomerization by a pseudouridine synthase enzyme. Pseudouridine is biosynthesized from uridine via the action of Ψ synthases.

57100-18-2
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$75.00/5 mg

1445-07-4
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$55.00/2.5mg

Yield:1445-07-4 3.2 g (85%)

Reaction Conditions:

with acetic anhydride in pyridine;ethyl acetate

Steps:

30 Peracetylated Pseudoisocytidine 2
Pseudoisocytidine (1) (2.5 g, 9 mmoles) was dissolved in 40 ml dry pyridine. Acetic anhydride (8.5 ml, 90 mmoles) was added and the mixture was stirred under argon for at least 4 hours at room temperature. The reaction can be monitored by HPLC (C18 column, buffer A: 0.1M TEAA, pH 7.5; buffer B: acetonitrile; gradient: 5-95%B over 20 minutes). The pyridine was removed under vacuum and the residual oil was dissolved in 500 ml of ethyl acetate. More ethyl acetate may be added to get a clear solution since the product has limited solubility in ethyl acetate. The organic phase was washed three times with brine and dried over anhydrous Na₂SO₄, filtered and the solvent removed. The white solid was recrystallized from ethyl acetate/hexane yielding 3.2 g (85%) of 2.

References:

Affymetrix, INC. US2005/3496, 2005, A1

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