scholarly journals Assessing the stereoselectivity of Serratia marcescens CECT 977 2,3-butanediol dehydrogenase

2017 ◽  
Vol 7 (9) ◽  
pp. 1831-1837 ◽  
Author(s):  
Rosario Médici ◽  
Hanna Stammes ◽  
Stender Kwakernaak ◽  
Linda G. Otten ◽  
Ulf Hanefeld
Keyword(s):  
Serratia Marcescens ◽  
Optically Active ◽  
Hydroxy Ketones ◽  
Butanediol Dehydrogenase

The meso-2,3-butanediol dehydrogenase from Serratia marcescens CECT 977 can produce several optically active hydroxy ketones from both the alcohol or ketone precursor.

scholarly journals Synthesis of α-hydroxy ketones and vicinal (R,R)-diols by Bacillus clausii DSM 8716T butanediol dehydrogenase

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12206-12216 ◽  
Author(s):  
Lukas Muschallik ◽  
Denise Molinnus ◽  
Melanie Jablonski ◽  
Carina Ronja Kipp ◽  
Johannes Bongaerts ◽  
...  
Keyword(s):  
Bacillus Clausii ◽  
Hydroxy Ketones ◽  
Vicinal Diols ◽  
Butanediol Dehydrogenase

Reduction of symmetric or asymmetric vicinal diketones with BcBDH leads to the synthesis of either α-hydroxyketones or vicinal diols.

Evidence for cellular control in the synthesis of acetoin or α-ketoisovaleric acid by microorganisms

1974 ◽  
Vol 20 (6) ◽  
pp. 805-811 ◽  
Author(s):  
E. B. Collins ◽  
R. A. Speckman
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Steady State ◽  
Serratia Marcescens ◽  
Lactobacillus Casei ◽  
Optically Active ◽  
Cell Free Extract ◽  
Data Support ◽  
A Cell ◽  
Cellular Control ◽  
Spent Media

Commercial α-acetolactate at pH 4.5 decarboxylated nonenzymatically (5 to 8%/h) to acetoin (69%) and diacetyl (31%), and an extract of Streptococcus diacetilactis 18-16 produced α-acetolactate (in addition to acetoin and diacetyl) from pyruvate in the presence of TPP and MgSO4. Nevertheless, α-acetolactate was not dispersed into media by any of four microorganisms (S. diacetilactis, strains 18-16 and DRC1, Saccharomyces cerevisiae 299, and Lactobacillus casei 393) that produced diacetyl and acetoin or by one (Serratia marcescens) that produced only acetoin. Lactobacillus casei and S. diacetilactis 18-16 produced unknown compounds that falsely indicated the presence of α-acetolactate when tests were made without separating acetoin and diacetyl from other components of the spent media. The production of acetoin by S. diacetilactis 18-16 was not inhibited by valine, the acetoin produced by this organism was optically active (+101.0°), and a cell-free extract of S. marcescens did not produce diacetyl while producing a large amount of acetoin. Data support the conclusion that the conversion of pyruvate to acetoin by some microorganisms and to α-ketoisovaleric acid by others is enzymatic and under cellular control, resulting in the synthesis of only steady-state amounts of enzymatically bound α-acetolactate in each of the pathways.

Catalytic enantioselective Amadori–Heyns rearrangement of racemic α-hydroxy ketones with arylamines: synthesis of optically active α-arylamino ketones

2013 ◽  
Vol 49 (78) ◽  
pp. 8812 ◽  
Author(s):  
Angelo Frongia ◽  
Francesco Secci ◽  
Francesca Capitta ◽  
Pier Paolo Piras ◽  
Maria Luisa Sanna
Keyword(s):  
Optically Active ◽  
Hydroxy Ketones

ChemInform Abstract: Catalytic Enantioselective Amadori-Heyns Rearrangement of Racemic α-Hydroxy Ketones with Arylamines: Synthesis of Optically Active α-Arylamino Ketones.

ChemInform ◽  
2014 ◽  
Vol 45 (5) ◽  
pp. no-no
Author(s):  
Angelo Frongia ◽  
Francesco Secci ◽  
Francesca Capitta ◽  
Pier Paolo Piras ◽  
Maria Luisa Sanna
Keyword(s):  
Optically Active ◽  
Hydroxy Ketones

Synthesis and Characterisation of Bridged Morpholine Derivatives Fused to a Phenanthrene Ring System

2017 ◽  
Vol 41 (4) ◽  
pp. 210-215 ◽  
Author(s):  
H. Surya Prakash Rao ◽  
Satish Vijjapu
Keyword(s):  
Spectral Analysis ◽  
Ring System ◽  
Optically Active ◽  
Theoretical Studies ◽  
Stereoselective Reduction ◽  
Steric Interactions ◽  
Conformationally Restricted ◽  
Hydroxy Ketones ◽  
Morpholine Derivatives

The synthesis of conformationally restricted and facially biased bridged morpholine derivatives fused to a phenanthrene ring system was prepared in a three-step sequence involving: (i) Voight rearrangement; (ii) stereoselective reduction of ketone and (iii) iodine mediated cyclisation, the α-allyl-α-hydroxy-ketones gave the corresponding bridged N-substituted morpholines. One of the bridged morpholine derivatives fused to a phenanthrene ring system was optically active. The NMR spectral analysis and theoretical studies show that substitution on nitrogen prefers exo-orientation, possibly to avoid steric interactions with the phenanthrene moiety.

Applications of Optically Active Aryl Cyanohydrins in the Synthesis of α-Hydroxy Aldehydes, α-Hydroxy Ketones and β-Hydroxy Amines

1990 ◽  
Vol 43 (12) ◽  
pp. 2045 ◽  
Author(s):  
WR Jackson ◽  
HA Jacobs ◽  
GS Jayatilake ◽  
BR Matthews ◽  
KG Watson
Keyword(s):  
Optical Purity ◽  
Optically Active ◽  
Aryl Aldehydes ◽  
High Optical Purity ◽  
Hydroxy Ketones ◽  
Hydroxy Aldehydes

Cyanohydrins, prepared in high optical purity from aryl aldehydes, have been converted into α- hydroxy aldehydes, β- hydroxy ketones and β- hydroxy amines without any racemization and frequently with good stereoselectivity for the erythro-diastereoisomer (>90%) at the newly introduced stereogenic centre.

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