Enzymes in organic synthesis : VI scope and enantioselectivity of enzymatic hydrolyses of organosilyl-substituted esters

Jeso, B. De; Belair, Nathalie; Deleuze, Hervé; Rascle, Marie-Claude; Maillard, B.

doi:10.1016/s0040-4039(00)94593-3

Cited by 37 publications

(6 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The key step in the asymmetric synthesis of ( R )- 1 and ( S )- 1 is the enantioselective ester cleavage of the prochiral diethyl malonate 3 to give the corresponding monoethyl malonate ( R )- 4 (Scheme ) . Porcine liver esterase (EC 3.1.1.1) was used as the biocatalyst, and the product ( R )- 4 was isolated in 94% yield with an enantiomeric purity of 85% ee.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of the Nonproteinogenic Silicon-Containing α-Amino Acids (R)- and (S)-α-[(Trimethylsilyl)methyl]alanine§Dedicated to Professor Johann Weis on the occasion of his 65th birthday.

et al. 2009

View full text Add to dashboard Cite

The nonproteinogenic silicon-containing, R,R-disubstituted R-amino acids (R)-and (S)-2-amino-2-methyl-3-(trimethylsilyl)propanoic acid [(R)-and (S)-R-[(trimethylsilyl)methyl]alanine, (R)-1 and (S)-1] were synthesized by multistep syntheses, starting from diethyl malonate, and both were isolated with an enantiomeric purity of >99% ee. Compound rac-1 was also prepared. The key step of the asymmetric syntheses of (R)-1 and (S)-1 was an enantioselective enzyme-catalyzed (porcine liver esterase) ester cleavage of the prochiral substrate diethyl methyl[(trimethylsilyl)methyl]malonate. The absolute configurations of (R)-1 and (S)-1 were established by crystal structure analyses of (R)-1 and of its rhodium complex (S Rh ,R C )-16.

show abstract

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of the Nonproteinogenic Silicon-Containing α-Amino Acids (R)- and (S)-α-[(Trimethylsilyl)methyl]alanine§Dedicated to Professor Johann Weis on the occasion of his 65th birthday.

et al. 2009

View full text Add to dashboard Cite

show abstract

“…14b,4,5 Replacement of the aryl group with an alkyl chain such as butyl led to poor ee but gave good ee with the trimethylsilylmethyl chain. 4,6 The substrate with a mono R-alkyl chain that gave excellent enantiopurity was with the tert-butyl chain. 7 No results have been reported with diethyl butylmalonate (2).…”

Section: Resultsmentioning

confidence: 99%

“…Preparation of 2-Butylpropanedioic Acid Monoethyl Ester (6). A 100-L Buchi reactor was charged with diethyl butylmalonate (2, 3.07 kg; 14.18 mol) and ethanol (8.52 L).…”

Section: Methodsmentioning

confidence: 99%

An Efficient Synthesis of (R)-2-Butyl-3-hydroxypropionic Acid

Prashad

Har

et al. 2006

Org. Process Res. Dev.

View full text Add to dashboard Cite

An efficient synthesis of (R)-2-butyl-3-hydroxypropionic acid (1) via a classical resolution of (±)-2-butyl-3-hydroxypropionic acid (7) with (R)-α-methylbenzylamine is described. (±)-2-Butyl-3-hydroxypropionic acid (7) was readily available from diethyl butylmalonate (2) in two steps. Results on the enantioselective enzymatic hydrolysis of 2 with pig liver esterase and α-chymotrypsin towards 1 are also described.

show abstract

“…Citing a report by Wang et al [64] suggesting that trimethylsilyl substituted alcohols were not substrates for enzymatic esterification, De Jeso et al examined the hydrolysis of a series of trimethylsilyl-substituted monoesters (2-(trimethylsilyl)ethyl propionate, 3-(trimethylsilyl)propyl propionate, 3-(trimethylsilyl)propyl acetate, and 4-(trimethylsilyl)butyl acetate)) using pig liver esterase, pig liver lipase, horse liver acetonic powder and α-chymotrypsin [65]. Pig liver esterase processed both 2-(trimethylsilyl)ethyl propionate and 3-(trimethylsilyl)propyl propionate, while horse liver acetonic powder readily accepted all of the trimethylsilyl esters; α-chymotrypsin on the other hand, was less successful as it was found that these esters were not substrates for α-chymotrypsin.…”

Section: Free Enzymes and Organosilicon Compoundsmentioning

confidence: 99%

“…The pig liver esterase was only able to successfully convert 3-(trimethylsilyl)propyl acetate. A second set of results pertaining to the selective mono hydrolysis of selected diesters by pig liver esterase and horse liver acetonic powder revealed that yields were achievable in the range of 59-95% with the enantiomeric excesses ranging from 10-98% [65].…”

Section: Free Enzymes and Organosilicon Compoundsmentioning

confidence: 99%

Organosilicon Biotechnology

Frampton

Zelisko

2009

Silicon

View full text Add to dashboard Cite

Inspired by Nature, biocatalysis and biotechnology have quickly become burgeoning fields in silicon chemistry. From cell cultures to isolated enzymes researchers are exploring the use of biological systems to affect chemical transformations at or near silicon atoms. This review will examine the history of biotechnology as it pertains to organosilicon compounds (i.e., compounds with one or more Si-C bonds) and provide some insights into future directions for the field.

show abstract

Enzymes in organic synthesis : VI scope and enantioselectivity of enzymatic hydrolyses of organosilyl-substituted esters

Cited by 37 publications

References 14 publications

Asymmetric Synthesis of the Nonproteinogenic Silicon-Containing α-Amino Acids (R)- and (S)-α-[(Trimethylsilyl)methyl]alanine§Dedicated to Professor Johann Weis on the occasion of his 65th birthday.

Asymmetric Synthesis of the Nonproteinogenic Silicon-Containing α-Amino Acids (R)- and (S)-α-[(Trimethylsilyl)methyl]alanine§Dedicated to Professor Johann Weis on the occasion of his 65th birthday.

An Efficient Synthesis of (R)-2-Butyl-3-hydroxypropionic Acid

Organosilicon Biotechnology

Contact Info

Product

Resources

About