Amino acid catalyzed condensation of purines and pyrimidines with 2-deoxyribose.
Mild heating of aqueous mixtures containing 2-deoxyribose, amino compounds, and purines or pyrimidines produces derivatives of the purines and pyrimidines in high yield. Among the major products formed are 2,3-dideoxy-3-(1'-pyrimidino)pentose and 2,3-dideoxy-3-(9'-purino)pentose. The mechanism of the reaction includes amine-catalzyed dehydration of the alpha, beta positions of the sugar followed by addition of the purine or pyrimidine to the double bond. Rapid addition of purines and pyrimidines to alpha, beta-unsaturated carbonyl compounds (such as acrolin) is a general phenomenon which does not require an amine catalyst. While multiple derivatization of the purines will take place, the N-9 derivative is formed first.
D000596:Amino Acids; D055598:Chemical Phenomena; D002621:Chemistry; D003855:Deoxyribose; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011687:Purines; D011743:Pyrimidines; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000596:Amino Acids; D011687:Purines; D011743:Pyrimidines; D003855:Deoxyribose