Literature DB >> 23404623

Access to organometallic arylcobaltcorrins through radical synthesis: 4-ethylphenylcobalamin, a potential "antivitamin B(12)".

Markus Ruetz1, Carmen Gherasim, Karl Gruber, Sergey Fedosov, Ruma Banerjee, Bernhard Kräutler.   

Abstract

Locked B(12): 4-Ethylphenylcobalamin, a novel organometallic arylcobalamin, has been synthesized in a radical reaction. This vitamin B(12) antimetabolite features a strong Co-C bond, and represents a "locked" form of vitamin B(12) . It may be used in animal studies to induce functional vitamin B(12) deficiency artificially to help clarify still controversial issues related to the pathophysiology of vitamin B(12) deficiency.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID： 23404623      PMCID： PMC3843227          DOI： 10.1002/anie.201209651

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  22 in total

1.  Time-resolved spectroscopic studies of B(12) coenzymes: a comparison of the primary photolysis mechanism in methyl-, ethyl-, n-propyl-, and 5'-deoxyadenosylcobalamin.

Authors:  Allwyn G Cole; Laurie M Yoder; Joseph J Shiang; Neil A Anderson; Larry A Walker; Mark M Banaszak Holl; Roseanne J Sension
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

Review 2.  Chemistry and enzymology of vitamin B12.

Authors:  Kenneth L Brown
Journal:  Chem Rev       Date:  2005-06       Impact factor: 60.622

3.  Nitroxylcob(III)alamin: synthesis and X-ray structural characterization.

Authors:  Luciana Hannibal; Clyde A Smith; Donald W Jacobsen; Nicola E Brasch
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  The corrin moiety of coenzyme B12 is the determinant for switching the btuB riboswitch of E. coli.

Authors:  Sofia Gallo; Michael Oberhuber; Roland K O Sigel; Bernhard Kräutler
Journal:  Chembiochem       Date:  2008-06-16       Impact factor: 3.164

5.  Complex riboswitches.

Authors:  Ronald R Breaker
Journal:  Science       Date:  2008-03-28       Impact factor: 47.728

6.  More radical magic with B12: B12-catalyzed, light-induced cleavage of DNA.

Authors:  Bernhard Kräutler; Barbara Puffer
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-10       Impact factor: 15.336

7.  Properties and reactivity of chlorovinylcobalamin and vinylcobalamin and their implications for vitamin B12-catalyzed reductive dechlorination of chlorinated alkenes.

Authors:  Kevin M McCauley; Derek A Pratt; Scott R Wilson; Justin Shey; Theodore J Burkey; Wilfred A van der Donk
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

8.  A B12-responsive internal ribosome entry site (IRES) element in human methionine synthase.

Authors:  Sebastian Oltean; Ruma Banerjee
Journal:  J Biol Chem       Date:  2005-07-28       Impact factor: 5.157

9.  New insights into the pathophysiology of cobalamin deficiency.

Authors:  Giuseppe Scalabrino; Maddalena Peracchi
Journal:  Trends Mol Med       Date:  2006-05-11       Impact factor: 11.951

10.  Identification of the gene responsible for methylmalonic aciduria and homocystinuria, cblC type.

Authors:  Jordan P Lerner-Ellis; Jamie C Tirone; Peter D Pawelek; Carole Doré; Janet L Atkinson; David Watkins; Chantal F Morel; T Mary Fujiwara; Emily Moras; Angela R Hosack; Gail V Dunbar; Hana Antonicka; Vince Forgetta; C Melissa Dobson; Daniel Leclerc; Roy A Gravel; Eric A Shoubridge; James W Coulton; Pierre Lepage; Johanna M Rommens; Kenneth Morgan; David S Rosenblatt
Journal:  Nat Genet       Date:  2005-11-27       Impact factor: 38.330
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  12 in total

1.  Coordination chemistry controls the thiol oxidase activity of the B12-trafficking protein CblC.

Authors:  Zhu Li; Aranganathan Shanmuganathan; Markus Ruetz; Kazuhiro Yamada; Nicholas A Lesniak; Bernhard Kräutler; Thomas C Brunold; Markos Koutmos; Ruma Banerjee
Journal:  J Biol Chem       Date:  2017-04-25       Impact factor: 5.157

2.  Replacement of the Cobalt Center of Vitamin B12 by Nickel: Nibalamin and Nibyric Acid Prepared from Metal-Free B12  Ligands Hydrogenobalamin and Hydrogenobyric Acid.

Authors:  Christoph Kieninger; Klaus Wurst; Maren Podewitz; Maria Stanley; Evelyne Deery; Andrew D Lawrence; Klaus R Liedl; Martin J Warren; Bernhard Kräutler
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-02       Impact factor: 15.336

3.  Antivitamin B12 Inhibition of the Human B12 -Processing Enzyme CblC: Crystal Structure of an Inactive Ternary Complex with Glutathione as the Cosubstrate.

Authors:  Markus Ruetz; Aranganathan Shanmuganathan; Carmen Gherasim; Agnes Karasik; Robert Salchner; Christoph Kieninger; Klaus Wurst; Ruma Banerjee; Markos Koutmos; Bernhard Kräutler
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-23       Impact factor: 15.336

4.  Pathogenic mutations differentially affect the catalytic activities of the human B12-processing chaperone CblC and increase futile redox cycling.

Authors:  Carmen Gherasim; Markus Ruetz; Zhu Li; Stephanie Hudolin; Ruma Banerjee
Journal:  J Biol Chem       Date:  2015-03-25       Impact factor: 5.157

5.  Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light.

Authors:  Wan-Lei Yu; Zi-Gang Ren; Ke-Xing Ma; Hui-Qing Yang; Jun-Jie Yang; Haixue Zheng; Wangsuo Wu; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-06-15       Impact factor: 9.969

6.  Redox-Linked Coordination Chemistry Directs Vitamin B12 Trafficking.

Authors:  Ruma Banerjee; Harsha Gouda; Shubhadra Pillay
Journal:  Acc Chem Res       Date:  2021-04-02       Impact factor: 22.384

Review 7.  Cobalamin coenzyme forms are not likely to be superior to cyano- and hydroxyl-cobalamin in prevention or treatment of cobalamin deficiency.

Authors:  Rima Obeid; Sergey N Fedosov; Ebba Nexo
Journal:  Mol Nutr Food Res       Date:  2015-05-12       Impact factor: 5.914

8.  4-ethylphenyl-cobalamin impairs tissue uptake of vitamin B12 and causes vitamin B12 deficiency in mice.

Authors:  Elena Mutti; Markus Ruetz; Henrik Birn; Bernhard Kräutler; Ebba Nexo
Journal:  PLoS One       Date:  2013-09-20       Impact factor: 3.240

9.  Methylfolate Trap Promotes Bacterial Thymineless Death by Sulfa Drugs.

Authors:  Marissa B Guzzo; Hoa T Nguyen; Thanh H Pham; Monika Wyszczelska-Rokiel; Hieronim Jakubowski; Kerstin A Wolff; Sam Ogwang; Joseph L Timpona; Soumya Gogula; Michael R Jacobs; Markus Ruetz; Bernhard Kräutler; Donald W Jacobsen; Guo-Fang Zhang; Liem Nguyen
Journal:  PLoS Pathog       Date:  2016-10-19       Impact factor: 6.823

10.  Structure of the human transcobalamin beta domain in four distinct states.

Authors:  Joël S Bloch; Markus Ruetz; Bernhard Kräutler; Kaspar P Locher
Journal:  PLoS One       Date:  2017-09-14       Impact factor: 3.240
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