- Biosynthesis of the Fairy Chemicals, 2-Azahypoxanthine and Imidazole-4-carboxamide, in the Fairy Ring-Forming Fungus Lepista sordida
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Fairy rings resulting from a fungus-plant interaction appear worldwide. 2-Azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) were first isolated from the culture broth of one of the fairy ring-forming fungi, Lepista sordida. Afterward, a common metabolite of AHX in plants, 2-aza-8-oxohypoxanthine (AOH), was found in AHX-treated rice. The biosynthetic pathway of the three compounds that are named as fairy chemicals (FCs) in plants has been partially elucidated; however, that in mushrooms remains unknown. In this study, it was revealed that the carbon skeletons of AHX and ICA were constructed from Gly in L. sordida mycelia and the fungus metabolized 5-aminoimidazole-4-carboxamide (AICA) to both of the compounds. These results indicated that FCs were biosynthesized by a diversion of the purine metabolic pathway in L. sordida mycelia, similar to that in plants. Furthermore, we showed that recombinant adenine phosphoribosyltransferase (APRT) catalyzed reversible interconversion not only between 5-aminoimidazole-4-carboxamide-1-β-d-ribofuranosyl 5′-monophosphate (AICAR) and AICA but also between ICA-ribotide (ICAR) and ICA. Furthermore, the presence of ICAR in L. sordida mycelia was proven for the first time by LC-MS/MS detection, and this study provided the first report that there was a novel metabolic pathway of ICA in which its ribotide was an intermediate in the fungus.
- Asakawa, Tomohiro,Choi, Jae-Hoon,Hirai, Hirofumi,Inai, Makoto,Ito, Akinobu,Kan, Toshiyuki,Kawagishi, Hirokazu,Kotajima, Mihaya,Ouchi, Hitoshi,Takemura, Hirohide,Tokuyama, Shinji,Wu, Jing
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- Imidazole compounds
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Imidazole compounds having adenosine deaminase inhibitory activity represented by formula (I) wherein R1is hydrogen, hydroxy, protected hydroxy, or aryl optionally substituted with suitable substituent(s); R2is hydrogen or lower alkyl; R3is hydroxy or protected hydroxy; R4is cyano, (hydroxy)iminoamino(lower)alkyl, carboxy, protected carboxy, heterocyclic group optionally substituted with amino, or carbamoyl optionally substituted with suitable substituent(s); and —A— is —Q— or —O—Q—, wherein Q is single bond or lower alkylene, provided that when R2is lower alkyl, then R1is hydroxy, protected hydroxy, or aryl optionally substituted with suitable substituent(s), its prodrug, or their salt. The compounds are useful for treating and/or preventing diseases for which adenosine is effective.
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Page column 8
(2008/06/13)
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- Derivatives of imidazole-4-carboxamide as substrates for various DNA polymerases
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A series of nucleotide analogs bearing imidazole 4-carboxamides as bases were synthetized. The ability of Klenow fragment of pol I and HIV-1 reverse transcriptase to use these 5'-triphosphate derivatives as substrates in DNA elongation reactions was investigated.
- Bec, Christine Le,Roux, Pascal,Buc, Henri,Pochet, Sylvie
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p. 1301 - 1302
(2007/10/03)
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- AN EFFICIENT METHOD FOR THE PREPARATION OF 4(5)- CYANOIMIDAZOLES
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We report herein a direct, cost-effective process for the preparation of 4(5)-cyanoimidazoles from the corresponding 4(5)-imidazolecarboxylates.
- Leone-Bay, Andrea,Glaser, Laurel
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p. 1409 - 1412
(2007/10/02)
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