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[将[5'-3H]核黄素转化为5,6-二甲基苯并咪唑]

[Transformation of [5'-3H]riboflavin into 5,6-dimethylbenzimidazole].

作者信息

Kolonko B, Hörig J A, Renz P

机构信息

Institut für Biologische Chemie und Ernährungswissenschaft Universität Hohenheim, Stuttgart, Bundesrepublik Deutschland.

出版信息

Z Naturforsch C J Biosci. 1992 Mar-Apr;47(3-4):171-6. doi: 10.1515/znc-1992-3-401.

DOI:10.1515/znc-1992-3-401
PMID:1590885
Abstract

The 5,6-dimethylbenzimidazole unit of vitamin B12 is formed from riboflavin via FMN in aerobic and some aerotolerant bacteria. Thereby C-1' of the ribityl side chain gets C-2 of 5,6-dimethylbenzimidazole. Experiments with homogenates of Propionibacterium shermanii on the fate of C-atoms 2' to 5' of the ribityl side chain of riboflavin in this transformation are reported. It was found that [5'-3H]riboflavin leads to radioactive sugar phosphates. These were isolated, dephosphorylated, and separated. Thus 3H-D-fructose and 3H-D-glucose were detected. The degradation of 3H-D-glucose revealed that 14 per cent of the total radioactivity was located in C-1, and 86 per cent in C-6. This indicates that during 5,6-dimethylbenzimidazole biosynthesis a three carbon unit is formed from the ribityl side chain of riboflavin.

摘要

在需氧和一些耐氧细菌中,维生素B12的5,6-二甲基苯并咪唑单元由核黄素经黄素单核苷酸形成。由此,核糖醇侧链的C-1'得到5,6-二甲基苯并咪唑的C-2。报道了关于谢氏丙酸杆菌匀浆在这种转化中核黄素核糖醇侧链C-2'至C-5'碳原子命运的实验。发现[5'-3H]核黄素会产生放射性糖磷酸酯。这些被分离、去磷酸化并分开。由此检测到3H-D-果糖和3H-D-葡萄糖。3H-D-葡萄糖的降解表明,总放射性的14%位于C-1,86%位于C-6。这表明在5,6-二甲基苯并咪唑生物合成过程中,一个三碳单元由核黄素的核糖醇侧链形成。

相似文献

1
[Transformation of [5'-3H]riboflavin into 5,6-dimethylbenzimidazole].[将[5'-3H]核黄素转化为5,6-二甲基苯并咪唑]
Z Naturforsch C J Biosci. 1992 Mar-Apr;47(3-4):171-6. doi: 10.1515/znc-1992-3-401.
2
Biosynthesis of vitamin B12. Transformation of riboflavin 2H-labeled in the 1'R position of 1'S position into 5,6-dimethylbenzimidazole.维生素B12的生物合成。1'S位1'R位置标记有2H的核黄素向5,6-二甲基苯并咪唑的转化。
Eur J Biochem. 1992 Aug 1;207(3):981-5. doi: 10.1111/j.1432-1033.1992.tb17133.x.
3
Biosynthesis of vitamin B12. Some properties of the 5,6-dimethylbenzimidazole-forming system of Propionibacterium freudenreichii and Propionibacterium shermanii.维生素B12的生物合成。费氏丙酸杆菌和谢氏丙酸杆菌中5,6-二甲基苯并咪唑形成系统的一些特性。
Eur J Biochem. 1980 Apr;105(3):587-92. doi: 10.1111/j.1432-1033.1980.tb04536.x.
4
Biosynthesis of the dimethylbenzene moiety of riboflavin and dimethylbenzimidazole: evidence for the involvement of C-1 of a pentose as a precursor.核黄素和二甲基苯并咪唑中二甲基苯部分的生物合成:戊糖的C-1作为前体参与的证据。
Biochemistry. 1977 Feb 8;16(3):526-31. doi: 10.1021/bi00622a029.
5
Nonenzymatic transformation of riboflavin into 5,6-dimethylbenzimidazole.
Z Naturforsch C Biosci. 1977 Jul-Aug;32(7-8):523-7. doi: 10.1515/znc-1977-7-808.
6
Biosynthesis of vitamin B12. Formation of free 5,6-dimethylbenzimidazole and alpha-ribazole from riboflavin by Propionibacterium freudenreichii.
FEBS Lett. 1977 Aug 15;80(2):337-9. doi: 10.1016/0014-5793(77)80470-5.
7
[Transformation of riboflavin into the 5,6-dimethylbenzimidazole part of vitamin B 12 ].
Hoppe Seylers Z Physiol Chem. 1972 May;353(5):747-8.
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[5-15N]Riboflavin as precursor in the biosynthesis of the 5,6-dimethylbenzimidazole moiety of vitamin B12. A study by 1H and 15N magnetic resonance spectroscopy.[5-¹⁵N]核黄素作为维生素B12中5,6-二甲基苯并咪唑部分生物合成的前体。一项通过¹H和¹⁵N磁共振波谱进行的研究。
J Biol Chem. 1978 Oct 25;253(20):7410-4.
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Biosynthesis of cobalamin in Salmonella typhimurium: transformation of riboflavin into the 5,6-dimethylbenzimidazole moiety.
Arch Microbiol. 1998 Dec;171(1):66-8. doi: 10.1007/s002030050679.
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[Flavin pool in Propionibacterium shermanii and the formation of corrinoids by bacterial cultures].[谢氏丙酸杆菌中的黄素池与细菌培养物中类咕啉的形成]
Mikrobiologiia. 1978 May-Jun;47(3):451-5.

引用本文的文献

1
BluB cannibalizes flavin to form the lower ligand of vitamin B12.BluB分解黄素以形成维生素B12的下部配体。
Nature. 2007 Mar 22;446(7134):449-53. doi: 10.1038/nature05611.
2
Single-enzyme conversion of FMNH2 to 5,6-dimethylbenzimidazole, the lower ligand of B12.单酶将黄素单核苷酸还原酶(FMNH2)转化为5,6-二甲基苯并咪唑,即维生素B12的下侧配体。
Proc Natl Acad Sci U S A. 2007 Feb 20;104(8):2921-6. doi: 10.1073/pnas.0609270104. Epub 2007 Feb 14.