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. 2023 Jul 11;10:1228763. doi: 10.3389/fmolb.2023.1228763

TABLE 1.

List of inhibitors (substrate, intermediate and product analogues) for riboflavin biosynthetic enzymes.

Enzymes Inhibitors References
3,4-dihydroxy-2-butanone 4-phosphate synthase (DHBPS) 4-phosphoerythronohydroxamic acid (4PEH) Islam et al. (2015)
GTP cyclohydrolase II (GCH II) Phosphomethylphosphonic acid guanylyl ester, GMPCPP Ren et al. (2005)
Pyrimidine deaminase/reductase Ribose-5-phosphate (RP5) Stenmark et al. (2007)
5-diamino-6-ribosylamino-2.4(1H,3H)-pyrimidinedione 5′-phosphate (AROPP) Chen et al. (2009)
Guanosine monophosphate (GMP) Dawson et al. (2013)
Lumazine synthase (LS) 1.5,6,7-Tetrahydro-6,7-dioxo-9-day-ribitylaminolumazines bearing alkyl phosphate Substituents (Ribitylamino)uracils bearing fluorosulfonyl, sulfonic Acid, and carboxylic Acid Cushman et al. (2005)
2,6-dioxo-(1H,3H)-9-N-ribitylpurine Cushman et al. (1997)
2,6-dioxo-(1H,3H)-8-aza-9-N-ribitylpurine Cushman et al. (1998)
6-(6-D-ribitylamino-2,4-dihydroxypyrimidine-5-yl)-1-hexylphosphonic acid Cushman et al. (1998)
9-day-Ribitylamino-1.3,7,9-tetrahydro-2,6,8-purinetriones bearing alkyl phosphate and α,α-difluorophosphonate Substituents Cushman et al. (1999b)
6-Carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-Oxo-8-ribitylaminolumazines Cushman et al. (2004)
1,4-bis [1-(9-D-ribityl-1,3,7-trihydropurine-2,6,8-trionyl)]butane Cushman et al. (2002a)
5-nitro-6-ribitylamino-2.4-(1H,3H) pyrimidinedione Cushman et al. (2001)
1,3,7-Trihydro-9-day-ribityl-2,4,8-purinetrione-7-yl (TS13) Ritsert et al. (1995)
3-(1,3-dihydro-9-day-ribityl-2,4,8-purinetrione-7-yl)propane 1-phosphate (TS44) Morgunova et al. (2007)
4-(6.7(5H,8H)-dioxo-8-day-ribityllumazine-5-yl)butane 1-phosphate (GJ43) [4-(6-chloro-2,4-dioxo-1,2,3,4 tetrahydropyrimidin-5-yl)butyl] phosphate (JC33) Morgunova et al. (2007)
3-Alkyl phosphate derivatives of 4.5,6,7-tetrahydro-1-day-ribityl-1H-pyrazolo [3,4-day]pyrimidinedione Morgunova et al. (2007)
N-[2,4-dioxo-6-day-ribitylamino-1.2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid derivatives Morgunova et al., 2007 Zhang et al., 2007 Zhang et al., 2008
Riboflavin synthase (RS) 1.5,6,7-Tetrahydro-6,7-dioxo-9-day-ribitylaminolumazines bearing alkyl phosphate Substituents Cushman et al. (2005)
Bis(6,7-dimethyl-8-D-ribityllumazines) Cushman et al. (1999a)
2,6-dioxo-(1H,3H)-9-N-ribitylpurine Cushman et al. (1998)
2,6-dioxo-(1H,3H)-8-aza-9-N-ribitylpurine Cushman et al. (1998)
9-day-Ribitylamino-1.3,7,9-tetrahydro-2,6,8-purinetriones bearing alkyl phosphate and α,α-difluorophosphonate Substituents Cushman et al. (2004)
5-phosphonoalkyl-6-D-ribitylaminopyrimidinediones (Amide derivatives) Cushman et al. (2002b)
N-[2,4-dioxo-6-day-ribitylamino-1.2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid derivatives Zhang et al. (2008)