Kinetic resolution of (R, S)-1,2-O-isopropylideneglycerol by esterification with dry mycelia of moulds

Romano, Diego; Ferrario, Virgilio F.; Molinari, Francesco; Gardossi, Lucia; Montero, Julio; Torre, Paolo; Converti, Attílio

doi:10.1016/j.molcatb.2006.04.009

Cited by 15 publications

(10 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, the enzymes display high stability in organic solvents. It has previously been shown that the catalytic activity for the esterification and ester hydrolysis of mycelia of different moulds from various species (Rhizopus oryzae, Rhizopus javanicus, Rhizopus liquefaciens and Aspergillus oryzae) is promising [13,16,18]. Similar results were obtained with cell-bound carboxyl-esterases from Bacillus coagulans [14,15] and Kluyveromyces marxianus [12].…”

Section: Introductionsupporting

confidence: 60%

“…The mycelia and other whole cells known for cell-bound carboxyl-esterase activity (the yeast Kluyveromyces marxianus and the bacterium Bacillus coagulans) were investigated as potential catalysts for the enantioselective hydrolysis of a novel class of tertalcohol esters, namely ␣,␣-disubstituted cyanohydrin acetates 1. All of the different strains were tested either as lyophilized mycelia or freshly prepared mycelia grown on medium [12][13][14][15][16]18].…”

Section: Resultsmentioning

confidence: 99%

“…Fungal mycelia and cell-bound hydrolases are such a versatile source of new enzymes, that to date has not yet been fully explored [12][13][14][15][16]. Many microorganisms have cell-bound esterases and other hydrolases.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Microbial-catalysed resolution of sterically demanding cyanohydrins

Paravidino

Holt

Romano

et al. 2010

Journal of Molecular Catalysis B: Enzymatic

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Introductionsupporting

confidence: 60%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Microbial-catalysed resolution of sterically demanding cyanohydrins

Paravidino

Holt

Romano

et al. 2010

Journal of Molecular Catalysis B: Enzymatic

Self Cite

View full text Add to dashboard Cite

show abstract

“…A very different situation was observed when the resolution of racemic 1,2 -Oisopropylideneglycerol ( IPG or solketal) was studied [19] . In this case, the kinetics of the esterifi cation with butyric acid catalyzed by A. oryzae MIM and R. oryzae CBS 112.07 were investigated by carrying out independent batch tests on the commercially available R -and S -IPG (Table 6.4 ).…”

Section: Stereoselective Esterifi Cations Of Racemic Alcoholsmentioning

confidence: 99%

Direct Esterification with Dry Mycelia of Molds: A (Stereo)selective, Mild and Efficient Method for Obtaining Structurally Diverse Esters

Molinari

Romano

Gandolfi

et al. 2008

Modern Biocatalysis

Self Cite

View full text Add to dashboard Cite

Enzymatic reactions in organic media have been a major issue in the fi eld of biocatalysis over the last two decades. Carboxylesterases (mostly lipases) have been used in monophasic organic solution under controlled values of water activity ( a w ) for catalyzing ester formation: the reaction equilibrium can be shifted towards ester formation by interesterifi cation or transesterifi cation [1] . Direct esterifi cation is often hampered by water formation, which may increase a w , thus negatively infl uencing the equilibrium.Cell -bound enzymes are diffi cult to purify and are often not very stable outside their natural environment: as a consequence, only few data are available on cellassociated enzymes used as biocatalysts. However, by using dry whole cells, cellbound enzymes can be directly used as biocatalysts in organic solvents.Whole cell catalysts do not need immobilization, especially when mycelial micro -organisms are involved, since their morphological structure allows for easy fi ltration and re -utilization. Carboxylesterases bound to the mycelia of molds have been advantageously employed as biocatalysts in water and/or organic solvents: the fi rst report of the use of fungal mycelia in organic solvent dates back to 1978 [2] , followed by the work of Gancet and co -workers [3] . Here this chapter reports on the properties of mycelium -bound fungal carboxylesterases and their applications in fl avor ester production as well as in stereoselective esterifi cation. Screening and Microbiological AspectsDifferent lyophilized micro -organisms, ranging from bacteria (46 strains) to yeasts (42 strains) and molds (15 strains), were screened for the hydrolysis of a number of esters (acetate, butyrate, and caprylate) of geraniol and n -hexanol [4] .

show abstract

“…Both enantiomeric excess of substrate (ee S ) and the corresponding product (ee P ) can be accurately measured in enzyme-catalyzed kinetic resolutions (Xu et al 2004;Wielechowska and Plenkiewicz 2005;Zimmermann et al 2006;Kotik et al 2005;Romano et al 2006;Berti et al 2006), which make the determination of the concentration of enantiomers much simpler.…”

Section: Introductionmentioning

confidence: 99%

A simple method to determine concentration of enantiomers in enzyme-catalyzed kinetic resolution

Zheng

Shen

2007

Biotechnol Lett

View full text Add to dashboard Cite

Kinetic resolutions play important roles in industrial biotransformations for production of optical pure compounds from racemic substrates. A simple method, based on enantiomeric excess of both substrate (ee (S)) and the corresponding product (ee (P)), was developed for determination of concentration of enantiomers in kinetic resolution. Since only relative quantity (ee) was required in the proposed method, calibration and cumbersome quantitative sample handling can be avoided and analytical accuracy can be greatly improved.

show abstract

Kinetic resolution of (R, S)-1,2-O-isopropylideneglycerol by esterification with dry mycelia of moulds

Cited by 15 publications

References 25 publications

Microbial-catalysed resolution of sterically demanding cyanohydrins

Microbial-catalysed resolution of sterically demanding cyanohydrins

Direct Esterification with Dry Mycelia of Molds: A (Stereo)selective, Mild and Efficient Method for Obtaining Structurally Diverse Esters

A simple method to determine concentration of enantiomers in enzyme-catalyzed kinetic resolution

Contact Info

Product

Resources

About