Home / Articles / Methods of synthesis of deuterium-labelled lipids

Methods of synthesis of deuterium-labelled lipids

Natal'ya Aleksandrovna Bragina 1
Natal'ya Aleksandrovna Bragina
, 
Vladimir Viktorovich Chupin 1
Vladimir Viktorovich Chupin
1 M. V. Lomonosov Moscow State Academy of Fine Chemical Technology
10.1070/RC1997v066n11ABEH000369
Published 30 November 1996
Communication , Volume 66, Issue 11, 975-986
9
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Bragina N. A., Chupin V. V. Methods of synthesis of deuterium-labelled lipids // Russian Chemical Reviews. 1997. Vol. 66. No. 11. pp. 975-986.
GOST all authors (up to 50)
Copy cite
Bragina N. A., Chupin V. V. Methods of synthesis of deuterium-labelled lipids // Russian Chemical Reviews. 1997. Vol. 66. No. 11. pp. 975-986.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1997v066n11ABEH000369
UR - https://rcr.colab.ws/publications/10.1070/RC1997v066n11ABEH000369
TI - Methods of synthesis of deuterium-labelled lipids
T2 - Russian Chemical Reviews
AU - Bragina, Natal'ya Aleksandrovna
AU - Chupin, Vladimir Viktorovich
PY - 1997
DA - 1996/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 975-986
IS - 11
VL - 66
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1997_Bragina,
author = {Natal'ya Aleksandrovna Bragina and Vladimir Viktorovich Chupin},
title = {Methods of synthesis of deuterium-labelled lipids},
journal = {Russian Chemical Reviews},
year = {1997},
volume = {66},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1997v066n11ABEH000369},
number = {11},
pages = {975--986},
doi = {10.1070/RC1997v066n11ABEH000369}
}
MLA
Cite this
MLA
Copy cite
Bragina, Natal'ya Aleksandrovna, and Vladimir Viktorovich Chupin. “Methods of synthesis of deuterium-labelled lipids.” Russian Chemical Reviews, vol. 66, no. 11, Nov. 1997, pp. 975-986. https://rcr.colab.ws/publications/10.1070/RC1997v066n11ABEH000369.
Views / Visits / Downloads
15 / 15 / 2

Abstract

The review deals with the methods of synthesis of deuterium-labelled hydrophobic and hydrophilic synthons of lipid molecules and the routes to selectively and perdeuterated phospholipids and their analogues. Deuterium-labelled lipids are used to study the structural organisation and functioning of biological membranes including NMR studies and neutron diffraction of lipid–lipid and lipid–protein interactions. The bibliography includes 145 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
7.
Neutron Diffraction Studies on the Location of Water in Lecithin Bilayer Model Membranes
Zaccai G., Blasie J.K., Schoenborn B.P.
Proceedings of the National Academy of Sciences of the United States of America , 1975
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
1H‐NMR study of gramicidin A transmembrane ion channel
Arseniev A.S., Barsukov I.L., Bystrov V.F., Lomize A.L., Ovchinnikov Y.A.
FEBS Letters , 1985
13.
Conformational behavior of Escherichia coli OmpA signal peptides in membrane mimetic environments
Rizo J., Blanco F.J., Kobe B., Bruch M.D., Gierasch L.M.
Biochemistry , 1993
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
20.
Exchange reactions of carboxylic acid salts. Facile preparation of .alpha.-deuteriocarboxylic acids
Atkinson J.G., Csakvary J.J., Herbert G.T., Stuart R.S.
Journal of the American Chemical Society , 1968
24.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
26.
Molecular order in cis and trans unsaturated phospholipid bilayers
Seelig J., Waespe-Sarcevic N.
Biochemistry , 1978
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
Preparation of fully deuterated fatty acids by simple method
Hsiao C.Y., Ottaway C.A., Wetlaufer D.B.
Lipids , 1974
30.
Synthesis of deuterium and carbon-13 labelled lipids
Tulloch A.P.
Chemistry and Physics of Lipids , 1979
33.
Stereospecific Hydroxylation of Long Chain Compounds by a Species of Torulopsis
Heinz E., Tulloch A.P., Spencer J.F.
Journal of Biological Chemistry , 1969
34.
Synthesis of methyl 16-trideuteriohexadecanoate
Tulloch A.P.
Chemistry and Physics of Lipids , 1977
36.
Synthesis of [2S-2-2H]- and [2R-2-2H]hexadecanoic acids
Tulloch A.P.
Chemistry and Physics of Lipids , 1982
37.
Synthesis of methyl ω-deuterated tetradecanoate and hexadecanoate
Westerman P.W., Ghrayeb N.
Chemistry and Physics of Lipids , 1981
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
Synthesis of isotopically labeled saturated fatty acids.
DasGupta S.K., Rice D.M., Griffin R.G.
Journal of Lipid Research , 1982
41.
Deuterium-hydrogen exchange during the catalytic deuteration of methyl oleate
Rohwedder W.K., Bitner E.D., Peters H.M., Dutton H.J.
JAOCS, Journal of the American Oil Chemists' Society , 1964
42.
Dual-labeled technique for human lipid metabolism studies using deuterated fatty acid isomers
Emken E.A., Rohwedder W.K., Dutton H.J., Dougherty R., Iacono J.M., Mackin J.
Lipids , 1976
43.
Preparation of methyl cis-9,cis-12-octadecadienoate-16,16,17,17-d4
Adlof R.O., Emken E.A.
Chemistry and Physics of Lipids , 1981
44.
Synthesis of di-, tetra, and hexadeuterated 11-octadecenoates
Dejarlais W.J., Emken E.A.
Journal of Labelled Compounds and Radiopharmaceuticals , 1978
46.
The rhodium-catalyzed deuteration of unsaturated triglycerides
Adlof R.O.
JAOCS, Journal of the American Oil Chemists' Society , 1990
49.
Synthesis and characterization of [1-13C]-and d8-arachidonic acid
Do U.H., Sundaram M.G., Ramachandran S., Bryant R.W.
Lipids , 1979
50.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
52.
Labeled bile acids II: Methyl 3β-hydroxychol-5-en-24-oate, labeled with 13C and/or 2H
Byon C.Y., Gut M., Lai C.K.
Journal of Labelled Compounds and Radiopharmaceuticals , 1984
53.
54
R. Livingston
J. Phys. Chem. , 1941
54.
55
G. A. Bogdanovskii
1958
55.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
56.
Syntheses of geometric isomers of di-, tetra-, and hexadeuterated 12-octadecenoates and their triglycerides
Rakoff H., Emken E.A.
Journal of Labelled Compounds and Radiopharmaceuticals , 1978
59.
60
A. N. Terenin
Optika i Spektrosk. , 1956
60.
A direct synthesis of Z-trisubstituted allylic alcohols via the Wittig reaction
Sreekumar C., Darst K.P., Still W.C.
Journal of Organic Chemistry , 1980
62.
64
Chem. Zentr. II , 1931
63.
65
A. A. Krasnovskii
Biofizika , 1959
65.
Nuclear magnetic resonance investigation of the cytochrome oxidase-phospholipid interaction: a new model for boundary lipid
Kang S.Y., Gutowsky H.S., Hshung J.C., Jacobs R., King T.E., Rice D., Oldfield E.
Biochemistry , 1979
66.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1946
67.
69
B. Commoner
1958
68.
Phospholipid head groups as sensors of electric charge in membranes
Seelig J., MacDonald P.M., Scherer P.G.
Biochemistry , 1987
70.
A total synthesis of phosphatidylcholines
Aneja R., Chadha J.S.
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism , 1971
72.
Improved method for the synthesis of phosphatidylcholines.
Harbison G.S., Griffin R.G.
Journal of Lipid Research , 1984
73.
THE SYNTHESIS OF ETHANOLAMINE-1-C14
Douglas D.E., Burditt A.M.
Canadian Journal of Chemistry , 1955
76.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
77.
Improved synthesis of choline phospholipids
Brockerhoff H., Ayengar N.K.
Lipids , 1979
78.
Lipid polymorphism and the functional roles of lipids in biological membranes.
Cullis P.R., De Kruijff B.
Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes , 1979
79.
Structure of the inverted hexagonal (HII) phase, and non-lamellar phase transitions of lipids
Seddon J.M.
Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes , 1990
80.
THE METABOLISM OF 2-CARBON COMPOUNDS RELATED TO GLYCINE
Weissbach A., Sprinson D.B.
Journal of Biological Chemistry , 1953
82.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
88.
Synthesis of asymmetrically deuterated glycerol and dibenzyl glyceraldehyde via boronic esters
Matteson D.S., Kandil A.A., Soundararajan R.
Journal of the American Chemical Society , 1990
89.
Determination of conformational properties of glycolipid head groups by deuterium NMR of oriented multibilayers
Jarrell H.C., Jovall P.A., Giziewicz J.B., Turner L.A., Smith I.C.
Biochemistry , 1987
90.
Steric course of the reactions catalyzed by 5-enolpyruvylshikimate-3-phosphate synthase, chorismate mutase, and anthranilate synthase
Asano Y., Lee J.J., Shieh T.L., Spreafico F., Kowal C., Floss H.G.
Journal of the American Chemical Society , 1985
91.
Clavulanic acid biosynthesis: the stereochemical course of β-lactam formation from chiral glycerol
Townsend C.A., Mao S.
Journal of the Chemical Society Chemical Communications , 1987
92.
Synthesis of L-serine stereospecifically labelled at C-3 with deuterium
Gani D., Young D.W.
Journal of the Chemical Society Perkin Transactions 1 , 1983
95.
The dependence of glyceroglycolipid orientation and dynamics on head-group structure
Jarrell H.C., Wand A.J., Giziewicz J.B., Smith I.C.
Biochimica et Biophysica Acta - Biomembranes , 1987
97.
Regio- and stereo-selectively deuteriated sialyl glycerolipids for dynamic studies by 2H NMR spectroscopy
Roy R., Letellier M., Fenske D., Jarrell H.C.
Journal of the Chemical Society Chemical Communications , 1990
98.
Head-group orientation of a glycolipid analog from deuterium NMR data
Ram P., Prestegard J.H.
Journal of the American Chemical Society , 1988
100.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
101.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
102.
106
F. Fichter
Helv. Chim. Acta , 1927
103.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
104.
Recent developments in the chemistry of phospholipids
Slotboom A.J., Bonsen P.P.
Chemistry and Physics of Lipids , 1970
105.
Glycerophospholipid synthesis: improved general method and new analogs containing photoactivable groups.
Gupta C.M., Radhakrishnan R., Khorana H.G.
Proceedings of the National Academy of Sciences of the United States of America , 1977
108.
Synthesis of lecithins by acylation of O-(sn-glycero-3-phosphoryl) choline with fatty acid anhydrides
Robles E.C., Van Den Berg D.
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism , 1969
109.
A novel synthesis of spin label derivatives of phosphatidylcholine.
Boss W.F., Kelley C.J., Landsberger F.R.
Analytical Biochemistry , 1975
110.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
112.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
114.
A Simple Chemical Method for Labelling Phosphatidylcholine and Sphingomyelin in the Choline Moiety
STOFFEL W., LEKIM D., SANG TSCHUNG T.
Hoppe-Seyler´s Zeitschrift für physiologische Chemie , 1971
115.
Glycophorin facilitates the transbilayer movement of phosphatidylcholine in vesicles
De Kruijff B., Van Zoelen E.J., Van Deenen L.L.
Biochimica et Biophysica Acta - Biomembranes , 1978
116.
Phospholipid synthesis: Oxazaphospholanes and dioxaphospholanes as intermediates
Eibl H.
Proceedings of the National Academy of Sciences of the United States of America , 1978
117.
Interaction of phospholipase A2 with micellar interfaces. Role of the N-terminal region
Van Dam-Mieras M.C., Slotboom A.J., Pieterson W.A., De Haas G.H.
Biochemistry , 1975
118.
Physicochemical studies of the protein-lipid interactions in melittin-containing micelles
Lauterwein J., Bösch C., Brown L.R., Wüthrich K.
Biochimica et Biophysica Acta - Biomembranes , 1979
119.
Two-dimensional 1H-NMR studies of phospholipase-A2-inhibitor complexes bound to a micellar lipid-water interface
DEKKER N., PETERS A.R., SLOTBOOM A.J., BOELENS R., KAPTEIN R., DIJKMAN R., HAAS G.
FEBS Journal , 1991
123.
Role of sterols in membranes
Nes W.R.
Lipids , 1974
124.
The function of sterols in membranes.
Demel R.A., De Kruyff B.
Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes , 1976
125.
Synthesis of [26,27-2H6] cholesterol and derivatives substituted in the side chain
Kirk D.N., Varley M.J., Makin H.L., Trafford D.J.
Journal of the Chemical Society Perkin Transactions 1 , 1983
130.
Regulation of lipid polymorphism is essential for the viability of phosphatidylethanolamine-deficient Escherichia coli cells.
Rietveld A.G., Chupin V.V., Koorengevel M.C., Wienk H.L., Dowhan W., de Kruijff B.
Journal of Biological Chemistry , 1994
134.
Molecular order in acholeplasma laidlawii membranes as determined by deuterium magnetic resonance of biosynthetically-incorporated specifically-labelled lipids
Stockton G.W., Johnson K.G., Butler K.W., Polnaszek C.F., Cyr R., Smith I.C.
Biochimica et Biophysica Acta - Biomembranes , 1975
135.
Deuterium NMR study of lipid organisation in Acholeplasma laidlawii membranes
STOCKTON G.W., JOHNSON K.G., BUTLER K.W., TULLOCH A.P., BOULANGER Y., SMITH I.C., DAVIS J.H., BLOOM M.
Nature , 1977
136.
Orientational order of unsaturated lipids in the membranes of Acholeplasma laidlawii as observed by 2H-NMR.
Rance M., Jeffrey K.R., Tulloch A.P., Butler K.W., Smith I.C.
Biochimica et Biophysica Acta - Biomembranes , 1980
137.
A 2H-NMR study of Acholeplasma laidlawii membranes highly enriched in myristic acid
Jarrell H.C., Butler K.W., Byrd R.A., Deslauriers R., Ekiel I., Smith I.C.
Biochimica et Biophysica Acta - Biomembranes , 1982
139.
Mass spectrometry of lipids labeled with stable isotopes.
Rohwedder W.K.
Progress in Lipid Research , 1985
140.
Deuterium NMR evaluation of the positional distribution of low levels of deuterium in the presence of Eu(fod)3
Pfeffer P.E., Foglia T.A., Barr P.A., Obenauf R.H.
Journal of Organic Chemistry , 1978
141.
Deuterium isotope effects on 13C chemical shifts in long-chain aliphatic compounds
Tulloch A.P., Mazurek M.
Journal of the Chemical Society Chemical Communications , 1973