- Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure
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Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.
- Coady, Tracey M.,Coffey, Lee V.,O'Reilly, Catherine,Lennon, Claire M.
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supporting information
p. 1108 - 1116
(2015/02/19)
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- Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates
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Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-δ-lactone and L-mannonic acid-γ-lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1,3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone.
- Song, Jie,Hollingsworth, Rawle I.
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p. 387 - 391
(2007/10/03)
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- De-novo Synthesis of Enantiomerically Pure Deoxy- and Aminodeoxyfuranosides
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(R)-3-Hydroxy-4-pentenoic acid (2), readily available by an aldol addition of doubly deprotonated (R)-2-hydroxy-1,2,2-triphenylethyl acetate (1) to acrolein, functions as a key intermediate for the synthesis of enantiomerically pure deoxy- and aminodeoxyf
- Graef, Silke,Braun, Manfred
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p. 1091 - 1098
(2007/10/02)
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