Literature summary for 4.1.1.23 extracted from

Goryanova, B.; Spong, K.; Amyes, T.L.; Richard, J.P.
Catalysis by orotidine 5-monophosphate decarboxylase: effect of 5-fluoro and 4-substituents on the decarboxylation of two-part substrates (2013), Biochemistry, 52, 537-546.

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Activating Compound

Activating Compound	Comment	Organism	Structure
HPO32-	decarboxylation of substrate analog 5'-deoxy-5-fluoroorotidine is activated. Decarboxylation of truncated substrate analog 1-(beta-D-erythrofuranosyl)-5-fluoroorotic acid is activated by exogenous phosphite dianion, but the 5-F substituent results in only a 0.8 kcal stabilization of the transition state for the phosphite-activated reaction	Saccharomyces cerevisiae

Organism

Organism	UniProt	Comment	Textmining
Saccharomyces cerevisiae	-	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
1-(beta-D-erythrofuranosyl)-5-fluoroorotic acid	truncated analog of the natural substrate orotidine 5'-monophosphate with enhanced reactivity towards decarboxylation. The vinyl carbanion-like transition state is stabilized by 3.5 kcal/mol by interactions with the 5-F substituent. Decarboxylation is activated by exogenous phosphite dianion, but the 5-F substituent results in only a 0.8 kcal stabilization of the transition state for the phosphite-activated reaction	Saccharomyces cerevisiae	1-(beta-D-erythrofuranosyl)-5-fluorouracil + CO2	-	?
5'-deoxy-5-fluoroorotidine	truncated analog of the natural substrate orotidine 5'-monophosphate with enhanced reactivity towards decarboxylation. The 4'-CH3 and 4'-CH2OH groups of 5'-deoxy-5-fluoroorotidine and orotidine, respectively, result in identical destabilizations of the transition state for the unactivated decarboxylation of 2.9 kcal/mol. By contrast, the 4'-CH3 group of 5'-deoxy-5-fluoroorotidine and the 4'-CH2OH group of orotidine result in very different 4.7 and 8.3 kcal/mol destabilizations of the transition state for the phosphite-activated decarboxylation	Saccharomyces cerevisiae	? + CO2	-	?

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Release 2023.1 (January 2023)