Details
| Original language | English |
|---|---|
| Pages (from-to) | 725-728 |
| Number of pages | 4 |
| Journal | Enzyme and microbial technology |
| Volume | 17 |
| Issue number | 8 |
| Publication status | Published - Aug 1995 |
| Externally published | Yes |
Abstract
The lipase-catalyzed acylation of 1,2-O-isopropylidene glycerol was studied. The products obtained were hydrolyzed to their corresponding 1-monostearoylglycerides. Different approaches were investigated, and for the transesterification of ethyl stearate with (rac)-1,2-O-isopropylidene glycerol 1 in various organic solvents the highest initial rates were found in n-heptane and n-dodecane. The direct esterification of 1 with stearic acid gave the highest conversion (84%). Variation of the alkyl residue of stearate led to a decrease in the initial rates in the order: ethyl → methyl ≈ propyl → butylstearate. An enantioselective reaction was found for the faster reacting R-enantiomer in the transesterification of 1 with ethyl stearate resulting in 11%ee for the product. To elucidate the reasons for the low stereoselectivity, reactions of R- and S-1,2-O-isopropylidene glycerol with ethyl stearate in n-heptane were carried out. The remaining activity of the lipase was between 50 and 85% after 50 to 600 h reaction time.
Keywords
- 1,2-O-isopropylidene glycerol, 2,2-Dimethyl-1,3-dioxolane-4-methanol, enantioselectivity, lipase, monoglyceride, monostearoylglycerol, organic solvent
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Chemical Engineering(all)
- Bioengineering
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Immunology and Microbiology(all)
- Applied Microbiology and Biotechnology
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In: Enzyme and microbial technology, Vol. 17, No. 8, 08.1995, p. 725-728.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Lipase-catalyzed synthesis of monostearoylglycerol in organic solvents from 1,2-O-isopropylidene glycerol
AU - Hess, R.
AU - Bornscheuer, U.
AU - Capewell, A.
AU - Scheper, T.
PY - 1995/8
Y1 - 1995/8
N2 - The lipase-catalyzed acylation of 1,2-O-isopropylidene glycerol was studied. The products obtained were hydrolyzed to their corresponding 1-monostearoylglycerides. Different approaches were investigated, and for the transesterification of ethyl stearate with (rac)-1,2-O-isopropylidene glycerol 1 in various organic solvents the highest initial rates were found in n-heptane and n-dodecane. The direct esterification of 1 with stearic acid gave the highest conversion (84%). Variation of the alkyl residue of stearate led to a decrease in the initial rates in the order: ethyl → methyl ≈ propyl → butylstearate. An enantioselective reaction was found for the faster reacting R-enantiomer in the transesterification of 1 with ethyl stearate resulting in 11%ee for the product. To elucidate the reasons for the low stereoselectivity, reactions of R- and S-1,2-O-isopropylidene glycerol with ethyl stearate in n-heptane were carried out. The remaining activity of the lipase was between 50 and 85% after 50 to 600 h reaction time.
AB - The lipase-catalyzed acylation of 1,2-O-isopropylidene glycerol was studied. The products obtained were hydrolyzed to their corresponding 1-monostearoylglycerides. Different approaches were investigated, and for the transesterification of ethyl stearate with (rac)-1,2-O-isopropylidene glycerol 1 in various organic solvents the highest initial rates were found in n-heptane and n-dodecane. The direct esterification of 1 with stearic acid gave the highest conversion (84%). Variation of the alkyl residue of stearate led to a decrease in the initial rates in the order: ethyl → methyl ≈ propyl → butylstearate. An enantioselective reaction was found for the faster reacting R-enantiomer in the transesterification of 1 with ethyl stearate resulting in 11%ee for the product. To elucidate the reasons for the low stereoselectivity, reactions of R- and S-1,2-O-isopropylidene glycerol with ethyl stearate in n-heptane were carried out. The remaining activity of the lipase was between 50 and 85% after 50 to 600 h reaction time.
KW - 1,2-O-isopropylidene glycerol
KW - 2,2-Dimethyl-1,3-dioxolane-4-methanol
KW - enantioselectivity
KW - lipase
KW - monoglyceride
KW - monostearoylglycerol
KW - organic solvent
UR - http://www.scopus.com/inward/record.url?scp=0029162321&partnerID=8YFLogxK
U2 - 10.1016/0141-0229(94)00126-C
DO - 10.1016/0141-0229(94)00126-C
M3 - Article
AN - SCOPUS:0029162321
VL - 17
SP - 725
EP - 728
JO - Enzyme and microbial technology
JF - Enzyme and microbial technology
SN - 0141-0229
IS - 8
ER -