TY - JOUR
T1 - Application of liposome membrane as the reaction field
T2 - A case study using the Horner–Wadsworth–Emmons reaction
AU - Shimanouchi, Toshinori
AU - Kitagawa, Yuki
AU - Kimura, Yukitaka
PY - 2019/1/1
Y1 - 2019/1/1
N2 - The properties of the liposome membrane as a reaction field were investigated by focusing on the Horner–Wadsworth–Emmons reaction as a case study. Use of the liposomes existing in the gel phase resulted in the enhanced activity of the substrates and furnished the products with same E/Z stereoselectivity as in the liposome-free system. The membrane environment in the gel phase most likely assisted the formation of adducts that induced selective generation of the E-isomer. The possible role of liposomes is to assist the proton removal from the reactant, rather than providing the basic interfacial environment.
AB - The properties of the liposome membrane as a reaction field were investigated by focusing on the Horner–Wadsworth–Emmons reaction as a case study. Use of the liposomes existing in the gel phase resulted in the enhanced activity of the substrates and furnished the products with same E/Z stereoselectivity as in the liposome-free system. The membrane environment in the gel phase most likely assisted the formation of adducts that induced selective generation of the E-isomer. The possible role of liposomes is to assist the proton removal from the reactant, rather than providing the basic interfacial environment.
KW - Horner–Wadsworth–Emmons reaction
KW - Liposome
KW - Phospholipid
KW - Reaction field
KW - Stereochemistry
UR - http://www.scopus.com/inward/record.url?scp=85062177929&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85062177929&partnerID=8YFLogxK
U2 - 10.1016/j.jbiosc.2019.01.015
DO - 10.1016/j.jbiosc.2019.01.015
M3 - Article
C2 - 30827857
AN - SCOPUS:85062177929
JO - Journal of Bioscience and Bioengineering
JF - Journal of Bioscience and Bioengineering
SN - 1389-1723
ER -