Isolation of Co 5'-deoxyadenosylcobinamide guanosine diphosphate, α-(2-methyladenyl)-Co 5'-deoxyadenosylcobamide, and Co methylcorrinoids from Clostridium thermoaceticum

Irion, E; Ljungdahl, Lars G.

doi:10.1021/bi00846a042

Cited by 21 publications

(8 citation statements)

References 8 publications

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“…This circumstance brings about some simplification in the biosynthetic scheme. Early attachment of this group also occurs in Nocardia rugosa (80,188) and in Clostridium ther- moaceticum (133,134). (g) No nucleotide-containing corrinoid with more than three free carboxyl groups could be isolated, in agreement with the earlier studies.…”

Section: (F)supporting

confidence: 88%

“…Evidence from many sources favors a different pathway of DBI incor poration in which GDP-cobinamide, discovered and characterized by Di Marco's group in N. rugosa (9, 10) participates. GDP-cobinamide is widely distributed in microorganisms (for example, see 30,134,206 ) in small con centrations along with cobin amide phosphate. GDP-cobinamide has an N ,8-glycosidic bond and hence it does not correspond to a complete corrinoid.…”

Section: From Cobinamide To the Completed Cob Amidementioning

confidence: 99%

See 1 more Smart Citation

Microbial Biosynthesis of B12-Like Compounds

Friedmann¹,

Cagen²

1970

Annu. Rev. Microbiol.

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Section: (F)supporting

confidence: 88%

Section: From Cobinamide To the Completed Cob Amidementioning

confidence: 99%

Microbial Biosynthesis of B12-Like Compounds

Friedmann¹,

Cagen²

1970

Annu. Rev. Microbiol.

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“…This resembles the situation in two other methanogens (Methanosarcina barkeri [4, 5, 191 and M . bryantii [l, 81, where derivatives of factor III also were found as the major corrinoid components. In contrast, in the acetogenic bacterium Clostridium thermoaceticurn the complete corrinoids were found to contain one of several nucleotide bases [42], with the derivatives of factor IIIm (Copcyano-5'-methoxybenzimidazolyl-cobamide) representing the main fractions.…”

Section: Discussionmentioning

confidence: 86%

The corrinoid from Methanobacterium thermoautotrophicum (Marburg strain). Spectroscopic structure analysis and identification as Cobeta-cyano-5'-hydroxybenzimidazolyl-cobamide (factor III)

Kräutler¹,

Moll

Thauer

1987

Eur J Biochem

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The corrinoids from Methanobacterium thermoautotrophicum were extracted as the Co-cyano derivative, which was isolated in crystalline form. A consistent set of spectroscopic data was acquired (ultraviolet/visible, circular dichroic, infrared, fast-atom-bombardment mass, 'H-NMR and ' 3C-NMR spectra), which allowed the structural analysis of this complete corrinoid. It was assigned the structure of the Coo-cyano-5'-hydroxybenzimidazolylcobamide and was identified with Friedrich and Bernhauer's 'factor 111' by comparison with an authentic sample.Methanogenic bacteria contain considerable amounts of cobalt corrinoids, structurally related to vitamin B12 [I -81. The function of these in bacterial metabolism in part still is unclear (see e.g. [9]). In Methanobacterium thermoautotrophicum, they participate in the assembly of the coenzyme-Abound acetyl group (bacterial 'acetate' synthesis) from Hz and COz and from other C1 components [lo, 111, possibly via an acetyl-corrinoid intermediate [12, 131. In Methanosarcina barkeri, corrinoid-containing proteins act as methyltransferases in CH4 formation from CH30H [14] and probably from CH,COOH [15]. They also play a second, less-defined role in the synthesis of CH4 [2, 16, 171.A thorough structural analysis of the corrinoid from M . thermoautotrophicum appeared in place, since recently a strongly stimulating effect of vitamin B12 was found on the synthesis of methane in Methanobacterium bryantii [16] and in M . thermoautotrophicum [17], presumed to be associated with the redox properties of the corrinoids [16, 171. Secondly, a cobamide-containing membrane protein complex was also isolated from M . thermoautotrophicum by Schulz and Fuchs [I 81, who suggested that this protein complex plays an 'important and novel role in the growth of methanogenic bacteria from C 0 2 and H2'.The corrinoids from two methanogens, M . bryantii [8] and M . barkeri [4, 5, 191, have already been analyzed in their Cocyano form and identified as Coo-cyano-5'-hydroxybenzimidazolyl-cobamide ('factor 111' [20]). This was achieved by ultraviolet/visible spectral analysis [8], by spectrophotometric comparison with authentic material [4] and by a correlation of the ultraviolet/vissible spectroscopic of the complete corrinoid, complemented by an HPLC and 'H-NMR spectroscopic analysis of hydrolytic degradation products that were identified as the mixture of isomeric cyano-aquocobinamides, as 5-hydroxybenzimidazole and 1-a-D-ribofu- ranosyl-5-hydroxybenzimidazole [5, 191).Factor 111 was first isolated and separated from other complete corrinoids from sewage sludge by Friedrich and Bernhauer [20]. Its structure then was assigned by ultraviolet/ visible spectral analysis, by degradation and identification of the fragments cobinamide and 5-hydroxybenzimidazole [21], as well as by locating the position of the phenolic hydroxysubstituent of the benzimidazole-nucleotide [22]. However, it appears that, to date, a consistent structural analysis of intact factor 111 by spectroscopic means is still lacking.We report...

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“…This places the enzyme in the Type II classification of Mildred Cohen (Biochemistry 2, 623 (1963)), i. e. among the enzymes in which the metal (M92+) forrhs a direct link with the enzyme. 6. The exchange of 32Pi into PEP or PP.…”

Section: +mentioning

confidence: 99%

A STUDY OF INTERMEDIARY METABOLISM WITH ISOTOPICALLY LABELED COMPOUNDS. Comprehensive Report, September 1966--September 1969.

Wood¹

1969

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Isolation of Co 5'-deoxyadenosylcobinamide guanosine diphosphate, α-(2-methyladenyl)-Co 5'-deoxyadenosylcobamide, and Co methylcorrinoids from Clostridium thermoaceticum

Cited by 21 publications

References 8 publications

Microbial Biosynthesis of B12-Like Compounds

Microbial Biosynthesis of B12-Like Compounds

The corrinoid from Methanobacterium thermoautotrophicum (Marburg strain). Spectroscopic structure analysis and identification as Cobeta-cyano-5'-hydroxybenzimidazolyl-cobamide (factor III)

A STUDY OF INTERMEDIARY METABOLISM WITH ISOTOPICALLY LABELED COMPOUNDS. Comprehensive Report, September 1966--September 1969.

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