Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 725-728 |
| Seitenumfang | 4 |
| Fachzeitschrift | Enzyme and microbial technology |
| Jahrgang | 17 |
| Ausgabenummer | 8 |
| Publikationsstatus | Veröffentlicht - Aug. 1995 |
| Extern publiziert | Ja |
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.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biotechnologie
- Chemische Verfahrenstechnik (insg.)
- Bioengineering
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Immunologie und Mikrobiologie (insg.)
- Angewandte Mikrobiologie und Biotechnologie
Zitieren
- Standard
- Harvard
- Apa
- Vancouver
- BibTex
- RIS
in: Enzyme and microbial technology, Jahrgang 17, Nr. 8, 08.1995, S. 725-728.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › 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 -