Acidic hydrolysis of 6-substituted 9-(2-deoxy-β-d-erythro- pentofuranosyl) purines and their 9-(1-alkoxyethyl) counter-parts: kinetics and mechanism.1
✍ Scribed by Mikko OivanXXXn; Harri Lönnberg; Xiao-xiong Zhou; Jyoti Chattopadhyaya
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 543 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
The rate constants for the hydrolysis of several rubrt mted 9-(2-deoxy-B-D-erythro-pentofurenosyl)purines end 9-(l-rlkoxyethvl)purines firm ii measured at different concentrrtionb of-oxoniua ion. The effects that varying the polar nature of the l lkoxy group exerts on the hydrolysis of unsubstituted 9-(l-rlkoxyethyl)purines are interpreted to indicate that the reection proceeds by a rate-limiting departure of the protonrted base moiety with a concomitent formation of an alkoxyethyl oxocarbenium ion. The same mechanism is applied to the hydrolysis of 9-(2-deoxy-B-D-or thro-pentofurrnosylypurines by -htituents corparing the influences that have on the reactivity of these compounds and their 9-(l-alkoxyethyl) counterparts.
No sign of rnomerization was detectqd. when the hydrolysis of 2'-deoxyadenosine was followed by H NMR spectroscopy.