Haem d1: stereoselective synthesis of the reduced form of its parent macrocycle using the original coupling strategy

1997 ◽  
pp. 2099-2110 ◽  
Author(s):  
Christopher J. Aucken ◽  
Finian J. Leeper ◽  
Alan R. Battersby
Keyword(s):  
Stereoselective Synthesis ◽  
Reduced Form ◽  
Coupling Strategy

ChemInform Abstract: Hydrostannylation-Cross-Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β-Unsaturated Esters.

ChemInform ◽  
2015 ◽  
Vol 46 (25) ◽  
pp. no-no
Author(s):  
Shinichi Fujiwara ◽  
Romain Cadou ◽  
Yousuke Yamaoka ◽  
Kiyosei Takasu ◽  
Ken-ichi Yamada
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Unsaturated Esters ◽  
Coupling Strategy

scholarly journals Oleate Hydratase from Lactobacillus rhamnosus ATCC 53103: A FADH2-Dependent Enzyme with Remarkable Industrial Potential

Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1051
Author(s):  
Stefano Serra ◽  
Davide De Simeis ◽  
Stefano Marzorati ◽  
Mattia Valentino
Keyword(s):  
Flavin Adenine Dinucleotide ◽  
Stereoselective Synthesis ◽  
Lactobacillus Rhamnosus ◽  
Reduced Form ◽  
Hydroxystearic Acid ◽  
Biochemical Processes ◽  
Simple Filtration ◽  
Water Glycerol ◽  
Oleate Hydratase

Recently, we described the preparation of the recombinant oleate hydratase from Lactobacillus rhamnosus ATCC 53103. We observed that the purified C-terminal His-tagged enzyme was completely inactive and the catalytic activity was partially restored only in presence of a large amount of flavin adenine dinucleotide (FAD). In the present work, we assess that this hydratase in the presence of the reduced form of flavin adenine dinucleotide (FADH2) is at least one hundred times as active as in the presence of the same concentration of FAD. By means of two different biochemical processes, we demonstrated unambiguously that oleate hydratase from Lactobacillus rhamnosus ATCC 53103 is a FADH2-dependent enzyme. As a first relevant application of this discovery, we devised a preparative procedure for the stereoselective synthesis of (R)-10-hydroxystearic acid. Accordingly, the hydration of oleic acid (up to 50 g/L) is performed on a multigram scale using the recombinant hydratase and FADH2 generated in situ as cofactor. The produced (R)-10-hydroxystearic acid (ee > 97%) precipitates from the reaction solvent (water/glycerol/ethanol) and is conveniently recovered by simple filtration (>90% yield).

scholarly journals Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

2019 ◽  
Vol 10 (11) ◽  
pp. 3223-3230 ◽  
Author(s):  
Paola Caramenti ◽  
Nina Declas ◽  
Romain Tessier ◽  
Matthew D. Wodrich ◽  
Jerome Waser
Keyword(s):  
Natural Products ◽  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Alkyl Aryl ◽  
Enol Ethers ◽  
Coupling Strategy

Highly stereoselective synthesis of Z-enamides and enol ethers at room temperature via an umpolung/cross coupling strategy applicable to drugs and natural products.

scholarly journals Hydrostannylation-Cross-Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β-Unsaturated Esters

2015 ◽  
Vol 2015 (6) ◽  
pp. 1264-1272 ◽  
Author(s):  
Shinichi Fujiwara ◽  
Romain Cadou ◽  
Yousuke Yamaoka ◽  
Kiyosei Takasu ◽  
Ken-ichi Yamada
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Unsaturated Esters ◽  
Coupling Strategy
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