Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid

Junzo Sunamoto; Mitsuaki Goto; Kiyoshi Iwamoto; Hiroki Kondo; Toshinori Sato

doi:10.1016/0005-2736(90)90346-P

Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid

Junzo Sunamoto, Mitsuaki Goto, Kiyoshi Iwamoto, Hiroki Kondo, Toshinori Sato

Research output: Contribution to journal › Article › peer-review

49 Citations (Scopus)

Abstract

The synthesis and characterization of an artificial boundary lipid, 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine (DDPC), are described. DDPC has two amide bonds instead of ester bonds of regular lecithins such as 1,2-dimyristoylphosphatidylcholine (DMPC). In differential scanning calorimetry (DSC) measurements, DDPC gave two endothermic peaks: one was at 18.0°C (ΔH = 10.74 kJ·mol^-1) and the other at 23.0°C (ΔH = 12.91 kJ·mol^-1). The former peak was sharp and considered to be the phase transition of the hydrocarbon region, while the latter was assigned to the melt of the hydrogen-belt formed by the amide groups of DDPC. Addition of DDPC to DMPC made the DMPC membrane less fluid in the region close to the surface, and significantly increased the reconstitution efficiency of glycophorin into the membrane. This effect of DDPC was much larger than that of naturally occurring lipid, sphingomyelin.

Original language	English
Pages (from-to)	209-219
Number of pages	11
Journal	BBA - Biomembranes
Volume	1024
Issue number	2
DOIs	https://doi.org/10.1016/0005-2736(90)90346-P
Publication status	Published - 1990 May 24
Externally published	Yes

Keywords

Boundary lipid, artificial
DSC
Fluorescence polarization
Lipid-protein interaction
Membrane fluidity

ASJC Scopus subject areas

Biophysics
Biochemistry
Cell Biology

Access to Document

10.1016/0005-2736(90)90346-P

Cite this

@article{8211a45e4d474bb7b55f9502c0ad0688,

title = "Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid",

abstract = "The synthesis and characterization of an artificial boundary lipid, 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine (DDPC), are described. DDPC has two amide bonds instead of ester bonds of regular lecithins such as 1,2-dimyristoylphosphatidylcholine (DMPC). In differential scanning calorimetry (DSC) measurements, DDPC gave two endothermic peaks: one was at 18.0°C (ΔH = 10.74 kJ·mol-1) and the other at 23.0°C (ΔH = 12.91 kJ·mol-1). The former peak was sharp and considered to be the phase transition of the hydrocarbon region, while the latter was assigned to the melt of the hydrogen-belt formed by the amide groups of DDPC. Addition of DDPC to DMPC made the DMPC membrane less fluid in the region close to the surface, and significantly increased the reconstitution efficiency of glycophorin into the membrane. This effect of DDPC was much larger than that of naturally occurring lipid, sphingomyelin.",

keywords = "Boundary lipid, artificial, DSC, Fluorescence polarization, Lipid-protein interaction, Membrane fluidity",

author = "Junzo Sunamoto and Mitsuaki Goto and Kiyoshi Iwamoto and Hiroki Kondo and Toshinori Sato",

year = "1990",

month = may,

day = "24",

doi = "10.1016/0005-2736(90)90346-P",

language = "English",

volume = "1024",

pages = "209--219",

journal = "BBA - Biomembranes",

issn = "0005-2736",

publisher = "Elsevier",

number = "2",

}

TY - JOUR

T1 - Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid

AU - Sunamoto, Junzo

AU - Goto, Mitsuaki

AU - Iwamoto, Kiyoshi

AU - Kondo, Hiroki

AU - Sato, Toshinori

PY - 1990/5/24

Y1 - 1990/5/24

N2 - The synthesis and characterization of an artificial boundary lipid, 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine (DDPC), are described. DDPC has two amide bonds instead of ester bonds of regular lecithins such as 1,2-dimyristoylphosphatidylcholine (DMPC). In differential scanning calorimetry (DSC) measurements, DDPC gave two endothermic peaks: one was at 18.0°C (ΔH = 10.74 kJ·mol-1) and the other at 23.0°C (ΔH = 12.91 kJ·mol-1). The former peak was sharp and considered to be the phase transition of the hydrocarbon region, while the latter was assigned to the melt of the hydrogen-belt formed by the amide groups of DDPC. Addition of DDPC to DMPC made the DMPC membrane less fluid in the region close to the surface, and significantly increased the reconstitution efficiency of glycophorin into the membrane. This effect of DDPC was much larger than that of naturally occurring lipid, sphingomyelin.

AB - The synthesis and characterization of an artificial boundary lipid, 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine (DDPC), are described. DDPC has two amide bonds instead of ester bonds of regular lecithins such as 1,2-dimyristoylphosphatidylcholine (DMPC). In differential scanning calorimetry (DSC) measurements, DDPC gave two endothermic peaks: one was at 18.0°C (ΔH = 10.74 kJ·mol-1) and the other at 23.0°C (ΔH = 12.91 kJ·mol-1). The former peak was sharp and considered to be the phase transition of the hydrocarbon region, while the latter was assigned to the melt of the hydrogen-belt formed by the amide groups of DDPC. Addition of DDPC to DMPC made the DMPC membrane less fluid in the region close to the surface, and significantly increased the reconstitution efficiency of glycophorin into the membrane. This effect of DDPC was much larger than that of naturally occurring lipid, sphingomyelin.

KW - Boundary lipid, artificial

KW - DSC

KW - Fluorescence polarization

KW - Lipid-protein interaction

KW - Membrane fluidity

UR - http://www.scopus.com/inward/record.url?scp=0025363139&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025363139&partnerID=8YFLogxK

U2 - 10.1016/0005-2736(90)90346-P

DO - 10.1016/0005-2736(90)90346-P

M3 - Article

C2 - 2354176

AN - SCOPUS:0025363139

SN - 0005-2736

VL - 1024

SP - 209

EP - 219

JO - BBA - Biomembranes

JF - BBA - Biomembranes

IS - 2

ER -

Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this