Recent advances in the chemistry of vitamin B12 and vitamin B12 model compounds: reductive cobalt-carbon bond cleavage reactions

1973 ◽  
Vol 33 (4) ◽  
pp. 545-566 ◽  
Author(s):  
G. N. Schrauzer
Keyword(s):  
Vitamin B12 ◽  
Bond Cleavage ◽  
Model Compounds ◽  
Carbon Bond ◽  
Recent Advances ◽  
Cleavage Reactions

scholarly journals Controlling Non-Native B12 Reactivity and Catalysis in the Transcription Factor CarH

2021 ◽  
Author(s):  
Xinhang Yang ◽  
Benjamin H. R. Gerroll ◽  
Yuhua Jiang ◽  
Amardeep Kumar ◽  
Yasmine S. Zubi ◽  
...  
Keyword(s):  
Transcription Factor ◽  
Vitamin B12 ◽  
Transcription Regulation ◽  
Bond Cleavage ◽  
Oxidative Addition ◽  
Mechanistic Studies ◽  
Organic Transformations ◽  
Carbon Bond ◽  
Wide Range ◽  
Hydride Elimination

Vitamin B12 derivatives catalyze a wide range of organic transformations, but B12-dependent enzymes are underutilized in biocatalysis relative to other metalloenzymes. In this study, we engineered a variant of the transcription factor CarH, called CarH*, that catalyzes styrene C-H alkylation with improved yield and selectivity relative to B12 itself. While the native function of CarH involves transcription regulation via AdoCbl Co(III)-carbon bond cleavage and β-hydride elimination to generate 4’,5’-didehydroadenosine, CarH*-catalyzed styrene alkylation proceeds via non-native oxidative addition and olefin addition coupled with a native-like β-hydride elimination. Mechanistic studies on this reaction echo findings from earlier studies on AdoCbl homolysis under strong cage conditions to suggest that CarH* can enable non-native radical chemistry with improved selectivity relative to B12 itself. These findings lay the groundwork for the development of B12-dependent enzymes as catalysts for a wide range of non-native transformations.

Cleavage of carbon–carbon bonds by radical reactions

2019 ◽  
Vol 48 (9) ◽  
pp. 2615-2656 ◽  
Author(s):  
Paramasivam Sivaguru ◽  
Zikun Wang ◽  
Giuseppe Zanoni ◽  
Xihe Bi
Keyword(s):  
Bond Cleavage ◽  
Radical Reactions ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Cleavage Reactions

This review provides insights into the in situ generated radicals triggered carbon–carbon bond cleavage reactions.

Anion Effects in Oxidative Aliphatic Carbon–Carbon Bond Cleavage Reactions of Cu(II) Chlorodiketonate Complexes

2016 ◽  
Vol 55 (14) ◽  
pp. 6916-6928 ◽  
Author(s):  
Sushma L. Saraf ◽  
Anna Miłaczewska ◽  
Tomasz Borowski ◽  
Christopher D. James ◽  
David L. Tierney ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Aliphatic Carbon ◽  
Cleavage Reactions

NOVEL CARBON–CARBON BOND CLEAVAGE REACTIONS OF α-AZOHYDROPEROXIDES

1982 ◽  
Vol 11 (10) ◽  
pp. 1607-1610 ◽  
Author(s):  
Masanori Utaka ◽  
Yuji Fujita ◽  
Akira Takeda
Keyword(s):  
Bond Cleavage ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Cleavage Reactions
Sign in / Sign up

Export Citation Format

Share Document