Enzyme in organischen Lösungsmitteln: Eigenschaften und Einsatz in der Synthese

Carrea, Giacomo; Riva, Sergio

doi:10.1002/1521-3757(20000703)112:13<2312::aid-ange2312>3.0.co;2-4

Cited by 65 publications

(14 citation statements)

References 319 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The stereocenter at C-2 was significantly distant from the acyl moiety that would have suffered alcoholysis cleavage (6 bonds), therefore it would have not been too surprising to observe low enzyme selectivity, if any. On the other hand, there are literature examples describing the successful resolutions of molecules carrying "remote" stereocenters, [12] and therefore the decision was made that it was worth trying.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases

et al. 2011

Self Cite

View full text Add to dashboard Cite

Abstract:The tandem use of laccases and lipases has been exploited for the simple preparative synthesis of enantiomerically enriched dimeric phenols. Laccase-catalyzed oxidation of isoeugenol (1) and vinylguaiacol (7) in biphasic systems gave as main products the racemic compounds 6 and 8, possessing structures similar to the b-5 dimers found in lignin. The synthesis of enantiomerically enriched 6 and 8 could be achieved by alcoholysis reactions catalyzed by commercial preparations of lipases in organic solvents. Although the E values were quite low (due to the "remote" stereocenters to be discriminated), the enantio-complementary behavior of the tested lipases allowed the simple isolation of the target compounds with ee up to 90%. It is noteworthy that these results have been achieved in vitro exploiting commercially available enzymes, without using the so-called "dirigent" proteins evolved by nature to direct the enantioselective coupling of phenols in vivo.

show abstract

Section: Resultsmentioning

confidence: 99%

“…[11] Here we show that enantiomerically enriched dimers can be more conveniently produced from their racemates (in turn synthesized by laccase-catalyzed oxidations) exploiting the well-known enantioselectivity of lipases, enzymes that are even able to discriminate enantiomers possessing the so-called "remote" stereocenters. [12]…”

Section: Laccasesmentioning

confidence: 99%

Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases

et al. 2011

Self Cite

View full text Add to dashboard Cite

show abstract

“…[23][24][25] In the present paper, the immobilization of CalB within p-NIPAM microgel particles was studied by changing water, as the solvent, with the organic solvents, isopropanol and n-hexane. Furthermore, the p-NIPAM polymer particles show a thermosensitive behaviour which can be used to control the uptake of the enzyme.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of lipase B within micron-sized poly-N-isopropylacrylamide hydrogel particles by solvent exchange

Gawlitza

Georgieva

et al. 2012

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

“…The separated compounds were detected photometrically at 210 nm with a photodiode array detector. The eluting solvent system was composed of 79.7% (vol/vol) water, 20% (vol/vol) acetonitrile, and 0.3% H 3 PO 4 . The usual flow rate was 0.7 ml/min.…”

mentioning

confidence: 99%

Cloning of a Nitrilase Gene from the CyanobacteriumSynechocystissp. Strain PCC6803 and Heterologous Expression and Characterization of the Encoded Protein

Heinemann¹,

Engels

Bürger³

et al. 2003

Appl Environ Microbiol

View full text Add to dashboard Cite

The gene encoding a putative nitrilase was identified in the genome sequence of the photosynthetic cyanobacterium Synechocystis sp. strain PCC6803. The gene was amplified by PCR and cloned into an expression vector. The encoded protein was heterologously expressed in the native form and as a His-tagged protein in Escherichia coli, and the recombinant strains were shown to convert benzonitrile to benzoate. The active enzyme was purified to homogeneity and shown by gel filtration to consist probably of 10 subunits. The purified nitrilase converted various aromatic and aliphatic nitriles. The highest enzyme activity was observed with fumarodinitrile, but also some rather hydrophobic aromatic (e.g., naphthalenecarbonitrile), heterocyclic (e.g., indole-3-acetonitrile), or long-chain aliphatic (di-)nitriles (e.g., octanoic acid dinitrile) were converted with higher specific activities than benzonitrile. From aliphatic dinitriles with less than six carbon atoms only 1 mol of ammonia was released per mol of dinitrile, and thus presumably the corresponding cyanocarboxylic acids formed. The purified enzyme was active in the presence of a wide range of organic solvents and the turnover rates of dodecanoic acid nitrile and naphthalenecarbonitrile were increased in the presence of water-soluble and water-immiscible organic solvents.

show abstract

Enzyme in organischen Lösungsmitteln: Eigenschaften und Einsatz in der Synthese

Cited by 65 publications

References 319 publications

Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases

Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases

Immobilization of lipase B within micron-sized poly-N-isopropylacrylamide hydrogel particles by solvent exchange

Cloning of a Nitrilase Gene from the CyanobacteriumSynechocystissp. Strain PCC6803 and Heterologous Expression and Characterization of the Encoded Protein

Contact Info

Product

Resources

About