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In ordinary chemical reactions of uracil, N(3) and N(1) or both are readily alkylated. For specific N(1) alkylation (e.g., glycosylation), N(3)H should be protected as a C(4)-O-silylated form, for example. It may be simply argued that the enzymes stereoselectively hold uracil so that only the N(1) site is available for a nucleophile.
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16944366885
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note
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a value for N(1)H in the N(3)H-protected (as an 4-enolether) 16 was reported to be 10.7 (ref 8).
-
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53
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16944362260
-
-
note
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- anion in the complexes. These interactions could be more dramatic in a lower dielectric media at an enzyme active site.
-
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54
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-
16944365450
-
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note
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+ but not from the amide moiety to yield the 20-like species (ref 20).
-
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55
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16944366611
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note
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2+-cyclen-attached dansylamide 15 was 5.0 (ref 20).
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