TY - JOUR
T1 - Detection of L-Proline-Catalyzed Michael Addition Reaction in Model Biomembrane
AU - Hirose, Masanori
AU - Sugisaki, Shigenori
AU - Suga, Keishi
AU - Umakoshi, Hiroshi
N1 - Funding Information:
Financial support by the Comision lnterministerial de Ciencia y Tecnologia of Spain (MAT 91 -1 152) is gratefully acknowledged. We also thank to Professor P.A. Jacobs for providing the Euro TS-1 sample.
Publisher Copyright:
© 2019 Masanori Hirose et al.
PY - 2019
Y1 - 2019
N2 - A method to detect the L-proline- (L-Pro-) catalyzed Michael addition reaction in model biomembranes has been established, using N-[p(2-benzimidazolyl)phenyl]maleimide and acetone as reactants. The effect of liposome membranes on this reaction was kinetically analyzed using fluorescence spectroscopy. The kinetics of the reaction were different from those of the constituent lipids of the liposomes. Zwitterionic 1,2-dipalmitoyl-sn-glycero-3-phosphocholine liposome, which is in the solid-ordered phase, had a better value of reaction rate, suggesting that the reaction rate constants of this reaction in liposome membrane systems could be regulated by the characteristics of the liposome membrane (i.e., the phase state and surface charge). Based on the results obtained, a plausible model of the L-Pro-catalyzed Michael addition reaction was discussed. The obtained results provide us with an easily detectable method to assess the reactivity of L-Pro in biological systems.
AB - A method to detect the L-proline- (L-Pro-) catalyzed Michael addition reaction in model biomembranes has been established, using N-[p(2-benzimidazolyl)phenyl]maleimide and acetone as reactants. The effect of liposome membranes on this reaction was kinetically analyzed using fluorescence spectroscopy. The kinetics of the reaction were different from those of the constituent lipids of the liposomes. Zwitterionic 1,2-dipalmitoyl-sn-glycero-3-phosphocholine liposome, which is in the solid-ordered phase, had a better value of reaction rate, suggesting that the reaction rate constants of this reaction in liposome membrane systems could be regulated by the characteristics of the liposome membrane (i.e., the phase state and surface charge). Based on the results obtained, a plausible model of the L-Pro-catalyzed Michael addition reaction was discussed. The obtained results provide us with an easily detectable method to assess the reactivity of L-Pro in biological systems.
UR - http://www.scopus.com/inward/record.url?scp=85062793656&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85062793656&partnerID=8YFLogxK
U2 - 10.1155/2019/4926435
DO - 10.1155/2019/4926435
M3 - Article
AN - SCOPUS:85062793656
SN - 2090-9063
VL - 2019
JO - E-Journal of Chemistry
JF - E-Journal of Chemistry
M1 - 4926435
ER -