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Chapter 23: Q32P (page 1097)

Question:When UMP is dissolved in T2O, exchange of T for H occurs at the 5-position. Propose a mechanism for this exchange.

Short Answer

Expert verified

When T2O attacks ribose phosphate, tritium adds to C5, lone pair of electrons on nitrogen atom moves to form a double bond between nitrogen and C6. The double bond between C5 and C6 is also shifted.

Step by step solution

01

Attack of at ribose-5-phosphate

When T2O attacks ribose phosphate, tritium adds to C5, lone pair of electrons on nitrogen atom moves to form a double bond between nitrogen and C6. The double bond between C5 and C6 is also shifted.

02

Step 2: Exchange of hydrogen with tritium

Now, the oxygen-tritium bond again attacks the hydrogen and it is lost. This bond is shifted and nitrogen regains its lone pair of electrons. Now at C5, hydrogen is replaced with tritium. The whole mechanism is shown below:

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