Nh2

FIGURE 18-16 Some enzyme cofactors important in one-carbon transfer reactions. The nitrogen atoms to which one-carbon groups are attached in tetrahydrofolate are shown in blue.

FIGURE 18-17 Conversions of one-carbon units on tetrahydrofolate.

The different molecular species are grouped according to oxidation state, with the most reduced at the top and most oxidized at the bottom. All species within a single shaded box are at the same oxidation state. The conversion of N5,N10-methylenetetrahydrofolate to N5-methyltetrahydrofolate is effectively irreversible. The enzymatic transfer of formyl groups, as in purine synthesis (see Fig. 22-33) and in the formation of formylmethionine in prokaryotes (Chapter 27), generally uses N10-formyltetrahydrofolate rather than N5-formyltetrahydrofolate. The latter species is significantly more stable and therefore a weaker donor of formyl groups. N5-formyltetrahydrofolate is a minor byproduct of the cyclohydrolase reaction, and can also form spontancously. Conversion of N5-formyltetrahydrofolate to N5, N10-methenyltetrahy-drofolate, requires ATP, because of an otherwise unfavorable equilibrium. Note that N5-formiminotetrahydrofolate is derived from histidine in a pathway shown in Figure 18-26.

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