Vitamin B12 and α-ribonucleosides

Chandra, Tilak; Brown, Kenneth L.

doi:10.1016/j.tet.2007.08.061

Cited by 20 publications

(8 citation statements)

References 129 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The peak areas corresponding to phenolyl-cobamide and p-cresolylcobamide both decreased by about 80 per cent, and a major peak with a retention time of 6.94 min, identical to that of rstb.royalsocietypublishing.org Phil Trans R Soc B 368: 20120320 authentic CN-Cbl, emerged (figure 5c). These findings provide evidence for guided biosynthesis [27], and cyanocobalamin was the major cobamide when 10 mM DMB was added to the growth medium.…”

Section: (D) Guided Biosynthesis Of Cobalamin In Sporomusamentioning

confidence: 58%

See 1 more Smart Citation

Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity

Yan

Yang

et al. 2013

Phil. Trans. R. Soc. B

132

101

View full text Add to dashboard Cite

Dehalococcoides mccartyi strains are corrinoid-auxotrophic Bacteria and axenic cultures that require vitamin B 12 (CN-Cbl) to conserve energy via organohalide respiration. Cultures of D. mccartyi strains BAV1, GT and FL2 grown with limiting amounts of 1 µg l −1 CN-Cbl quickly depleted CN-Cbl, and reductive dechlorination of polychlorinated ethenes was incomplete leading to vinyl chloride (VC) accumulation. In contrast, the same cultures amended with 25 µg l −1 CN-Cbl exhibited up to 2.3-fold higher dechlorination rates, 2.8–9.1-fold increased growth yields, and completely consumed growth-supporting chlorinated ethenes. To explore whether known cobamide-producing microbes supply Dehalococcoides with the required corrinoid cofactor, co-culture experiments were performed with the methanogen Methanosarcina barkeri strain Fusaro and two acetogens, Sporomusa ovata and Sporomusa sp. strain KB-1, as Dehalococcoides partner populations. During growth with H 2 /CO 2 , M. barkeri axenic cultures produced 4.2 ± 0.1 µg l −1 extracellular cobamide (factor III), whereas the Sporomusa cultures produced phenolyl- and p -cresolyl-cobamides. Neither factor III nor the phenolic cobamides supported Dehalococcoides reductive dechlorination activity suggesting that M. barkeri and the Sporomusa sp. cannot fulfil Dehalococcoides ' nutritional requirements. Dehalococcoides dechlorination activity and growth occurred in M. barkeri and Sporomusa sp. co-cultures amended with 10 µM 5′,6′-dimethylbenzimidazole (DMB), indicating that a cobalamin is a preferred corrinoid cofactor of strains BAV1, GT and FL2 when grown with chlorinated ethenes as electron acceptors. Even though the methanogen and acetogen populations tested did not produce cobalamin, the addition of DMB enabled guided biosynthesis and generated a cobalamin that supported Dehalococcoides ' activity and growth. Guided cobalamin biosynthesis may offer opportunities to sustain and enhance Dehalococcoides activity in contaminated subsurface environments.

show abstract

Section: (D) Guided Biosynthesis Of Cobalamin In Sporomusamentioning

confidence: 58%

“…The microbial synthesis of non-native cobamides in the presence of excess non-native lower ligand is known as guided biosynthesis [17,27,34]. Guided biosynthesis has been demonstrated with model organisms such as Propionibacterium shermanii, E. coli and Streptomyces griseus to obtain desired cobamides [17].…”

Section: Discussionmentioning

confidence: 99%

Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity

Yan

Yang

et al. 2013

Phil. Trans. R. Soc. B

132

101

View full text Add to dashboard Cite

show abstract

“…In contrast, less attention has been paid to investigations of backbone modified B 12 derivatives. 29,64,65 This is surprising since various Cbls with structural differences in the sugar-phosphate backbone are encountered in nature. 66,67 The mode of coordination at the "lower" face of Cbls controls cofactor binding to biomacromolecules as well as reactivity of the trans-located organometallic cobalt carbon bond.…”

Section: Backbone Modified B 12 Derivativesmentioning

confidence: 99%

Peptide B₁₂: emerging trends at the interface of inorganic chemistry, chemical biology and medicine

2013

View full text Add to dashboard Cite

“…For ribonucleosides the β configuration is almost major and the configuration remains minor [5]. Solid phase reactions play an important role in environmental friendliness, ease of handling, ease of product separation, as they are fast, selective, and cheaper.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α-ribonucleoside (Majority) by the Coupling of NP/KI and NP/I₂

Ouzebla

2020

EJCHEM

View full text Add to dashboard Cite

In this work we will demonstrate a method of preparing α-D-ribonucleosides using the solid-phase approach using the combination between natural phosphate doped with potassium iodide (NP/KI) and natural phosphate doped with iodine (NP/I2). All these derivatives ribonucleosides were prepared by N-glycosylation reaction between silylated bases and 1-O-acétyl-2,3,5-tri-O-benzoyl-β-D-ribofuranoside.

show abstract

Vitamin B12 and α-ribonucleosides

Cited by 20 publications

References 129 publications

Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity

Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity

Peptide B₁₂: emerging trends at the interface of inorganic chemistry, chemical biology and medicine

Synthesis of α-ribonucleoside (Majority) by the Coupling of NP/KI and NP/I₂

Contact Info

Product

Resources

About

Vitamin B12 and α-ribonucleosides

Cited by 20 publications

References 129 publications

Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity

Guided cobalamin biosynthesis supports Dehalococcoides mccartyi reductive dechlorination activity

Peptide B12: emerging trends at the interface of inorganic chemistry, chemical biology and medicine

Synthesis of α-ribonucleoside (Majority) by the Coupling of NP/KI and NP/I₂

Contact Info

Product

Resources

About

Peptide B₁₂: emerging trends at the interface of inorganic chemistry, chemical biology and medicine