Negative Charge at Amino Acid 149 Is the Molecular Determinant for Substrate Specificity of Lecithin:Cholesterol Acyltransferase for Phosphatidylcholine Containing 20-Carbon sn-2 Fatty Acyl Chains

Biochemistry

Volumn 42, Issue 47, 2003, Pages 13941-13949

  Zhao, Yue ^a   Wang, Jingchuan ^a,b   Gebre, Abraham K ^a   Chisholm, Jeffrey W ^a,c   Parks, John S ^a  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF FLORIDA HEALTH SCIENCE CENTER   (United States)

^c CV THERAPEUTICS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CARBON; CHOLESTEROL; ENZYMES; MUTAGENESIS; SUBSTITUTION REACTIONS; SUBSTRATES;

MOLECULAR DETERMINANTS;

AMINO ACIDS;

AMINO ACID; AMINO ACID 149; CARBON; CHOLESTEROL ACYLTRANSFERASE; FATTY ACID; PHOSPHATIDYLCHOLINE; UNCLASSIFIED DRUG;

ACCURACY; ANIMAL CELL; ARTICLE; CONTROLLED STUDY; ELECTRIC POTENTIAL; ENZYME ACTIVITY; EXPERIMENTAL TEST; HUMAN; HUMAN CELL; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; MONKEY; MUTATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN BINDING; RAT; REVERTANT;

ALANINE; AMINO ACID SUBSTITUTION; ANIMALS; CERCOPITHECUS AETHIOPS; CHO CELLS; COS CELLS; CRICETINAE; ELECTROSTATICS; FATTY ACIDS; GLUTAMIC ACID; HUMANS; HYDROPHOBICITY; KINETICS; PHOSPHATIDYLCHOLINE-STEROL O-ACYLTRANSFERASE; PHOSPHATIDYLCHOLINES; RATS; SUBSTRATE SPECIFICITY;

ANIMALIA;

EID: 0345275893     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi035460u     Document Type: Article

References (38)

1. Jonas, A. (1998) Regulation of lecithin cholesterol acyltransferase activity, Prog. Lipid Res. 37, 209-234.
2. Glomset, J. A., Janssen, E. T., Kennedy, R., and Dobbins, J. (1966) Role of plasma lecithin:cholesterol acyltransferase in the metabolism of high-density lipoproteins, J. Lipid Res. 7, 638-648.
3. Glomset, J. A. (1968) The plasma lecithin:cholesterol acyltransferase reaction, J. Lipid Res. 9, 155-167.
4. Fielding, C. J., Shore, V. G., and Fielding, P. E. (1972) A protein cofactor of lecithin:cholesterol acyltransferase, Biochem. Biophys. Res. Commun. 46, 1493-1498.
5. Fielding, C. J., and Fielding, P. E. (1995) Molecular physiology of reverse cholesterol transport, J. Lipid Res. 36, 211-228.
6. Hamilton, R. L., Williams, M. C., Fielding, C. J., and Havel, R. J. (1976) Discoidal bilayer structure of nascent high-density lipoproteins from perfused rat liver, J. Clin. Invest. 58, 667-680.
7. Babiak, J., Tamachi, H., Johnson, F. L., Parks, J. S., and Rudel, L. L. (1986) Lecithin:cholesterol acyltransferase-induced modifications of liver perfusate discoidal high-density lipoproteins from African green monkeys, J. Lipid Res. 27, 1304-1317.
8. Jonas, A., Zorich, N. L., Kezdy, K. E., and Trick, W. E. (1987) Reaction of discoidal complexes of apolipoprotein A-I and various phosphatidylcholines With lecithin cholesterol acyltransferase. Interfacial effects, J. Biol. Chem. 262, 3969-3974.
9. Pownall, H. J., Pao, Q., and Massey, J. B. (1985) Acyl chain and headgroup specificity of human plasma lecithin:cholesterol acyltransferase. Separation of matrix and molecular specificities, J. Biol. Chem. 260, 2146-2152.
10. Parks, J. S., Huggins, K. W., Gebre, A. K., and Burleson, E. R. (2000) Phosphatidylcholine fluidity and structure affect lecithin:cholesterol acyltransferase activity, J. Lipid Res. 41, 546-553.
11. Peelman, F., Verschelde, J. L., Vanloo, B., Ampe, C., Labeur, C., Tavernier, J., Vandekerckhove, J., and Rosseneu, M. (1999) Effects of natural mutations in lecithin:cholesterol acyltransferase on the enzyme structure and activity, J. Lipid Res. 40, 59-69.
12. Portman, O. W., and Sugano, M. (1964) Factors influencing the level and fatty acid specificity of the cholesterol esterification activity in human plasma, Arch. Biochem. Biophys. 105, 532-540.
13. Sgoutas, D. S. (1972) Fatty acid specificity of plasma phosphatidylcholine:cholesterol acyltransferase, Biochemistry 11, 293-296.
14. Grove, D., and Pownall, H. J. (1991) Comparative specificity of plasma lecithin:cholesterol acyltransferase from 10 animal species, Lipids 26, 416-420.
15. Liu, M., Bagdade, J. D., and Subbaiah, P. V. (1995) Specificity of lecithin:cholesterol acyltransferase and atherogenic risk: Comparative studies on the plasma composition and in vitro synthesis of cholesteryl esters in 14 vertebrate species, J. Lipid Res. 36, 1813-1824.
16. 2 and transacylase fatty acyl specificity, J. Biol. Chem. 272, 280-286.
17. Parks, J. S., Bullock, B. C., and Rudel, L. L. (1989) The reactivity of plasma phospholipids with lecithin:cholesterol acyltransferase is decreased in fish oil-fed monkeys, J. Biol. Chem. 264, 2545-2551.
18. Peelman, F., Vinaimont, N., Verhee, A., Vanloo, B., Verschelde, J. L., Labeur, C., Seguret-Mace, S., Duverger, N., Hutchinson, G., Vandekerckhove, J., Tavernier, J., and Rosseneu, M. (1998) A proposed architecture for lecithin cholesterol acyl transferase (LCAT): Identification of the catalytic triad and molecular modeling, Protein Sci. 7, 587-599.
19. Wang, J., Gebre, A. K., Anderson; R. A., and Parks, J. S. (1997) Cloning and in vitro expression of rat lecithin:cholesterol acyltransferase, Biochim. Biophys. Acta 1346, 207-211.
20. Chisholm, J. W., Gebre, A. K., and Parks, J. S. (1999) Characterization of C-terminal histidine tagged human recombinant lecithin:cholesterol acyltransferase, J. Lipid Res. 40, 1512-1519.
21. Huggins, K. W., Curtiss, L. K., Gebre, A. K., and Parks, J. S. (1998) Effect of long chain polyunsaturated fatty acids in the sn-2 position of phosphatidylcholine on the interaction with recombinant high-density lipoprotein apolipoprotein A-I, J. Lipid Res. 39, 2423-2431.
22. Bohm, G., Muhr, R., and Jaenicke, R. (1992) Quantitative-analysis of protein far UV circular-dichroism spectra by neural networks, Protein Eng. 5, 191-195.
23. Parks, J. S., and Gebre, A. K. (1997) Long chain polyunsaturated fatty acids in the sn-2 position of phosphatidylcholine decrease the stability of recombinant high-density lipoprotein apoA-I and the activation energy of lecithin:cholesterol acyltransferase reaction, J. Lipid Res. 38, 266-275.
24. Parks, J. S., Gebre, A. K., and Furbee, J. W., Jr. (1998) in Methods in Molecular Biology (Doolittle, M., and Reue, K., Eds.) pp 123-131, Humana Press, Totowa, NJ.
25. Green, N. M., Konieczny, L., Toms, E. J., and Valentine, R. C. (1971) The use of bifunctional biotinyl compounds to determine the arrangement of subunits in avidin, Biochem. J. 125, 781-791.
26. Bolin, D. J., and Jonas, A. (1994) Binding of lecithin:cholesterol acyltransferase to reconstituted high-density lipoproteins is affected by their lipid but not apolipoprotein composition, J. Biol. Chem. 269, 7429-7434.
27. Jin, L. H., Lee, Y. P., and Jonas, A. (1997) Biochemical and biophysical characterization of human recombinant lecithin: cholesterol acyltransferase, J. Lipid Res. 38, 1085-1093.
28. Pownall, H. J., Pao, Q., and Massey, J. B. (1985) Isolation and specificity of rat lecithin:cholesterol acyltransferase: comparison with the human enzyme using reassembled high-density lipoproteins containing ether analogs of phosphatidylcholine, Biochim. Biophys. Acta 833, 456-462.
29. Hida, Y., Furukawa, Y., Urano, T., Kim, H. J., and Kimura, S. (1993) Substrate specificity of rat plasma lecithin-cholesterol acyltransferase towards a molecular species of phosphatidylcholine, Biosci., Biotechnol. Biochem. 57, 1111-1114.
30. Peelman, F., Goethals, M., Vanloo, B., Labeur, C., Brasseur, R., Vandekerckhove, J., and Rosseneu, M. (1997) Structural and functional properties of the 154-171 wild-type and variant peptides of human lecithin-cholesterol acyltransferase, Eur. J. Biochem. 249, 708-715.
31. Peelman, F., Vanloo, B., Verschelde, J. L., Labeur, C., Caster, H., Taveirne, J., Verhee, A., Duverger, N., Vandekerckhove, J., Tavernier, J., and Rosseneu, M. (2001) Effect of mutations of N-and C-terminal charged residues on the activity of LCAT, J. Lipid Res. 42, 471-479.
32. Furbee, J. W., Jr., Francone, O. L., and Parks, J. S. (2001) Alteration of plasma HDL cholesteryl ester composition with transgenic expression of a point mutation (E149A) of human lecithin:cholesterol acyltransferase (LCAT), J. Lipid Res. 42, 1626-1635.
33. Kingsbury, K. J., Brett, C., Stovold, R., Chapman, A., Anderson, J., and Morgan, D. M. (1974) Abnormal fatty acid composition and human atherosclerosis, Postgraduate Medical Journal 50, 425-440.
34. Kingsbury, K. J., Stovold, R., Morgan, D. M., and Brett, C. G. (1969) The relationships between plasma cholesteryl polyunsaturated fatty acids, age and atherosclerosis, Postgrad. Med. J. 45, 591-601.
35. Parks, J. S., Johnson, F. L., Wilson, M. D., and Rudel, L. L. (1990) Effect of fish oil diet on hepatic lipid metabolism in nonhuman primates: lowering of secretion of hepatic triglyceride but not apoB, J. Lipid Res. 31, 455-466.
36. Wolfe, M. S., Sawyer, J. K., Morgan, T. M., Bullock, B. C., and Rudel, L. L. (1994) Dietary polyunsaturated fat decreases coronary artery atherosclerosis in a pediatric-aged population of African green monkeys, Arterioscler. Thromb. 14, 587-597.
37. Rudel, L. L., Parks, J. S., and Sawyer, J. K. (1995) Compared with dietary monounsaturated and saturated fat, polyunsaturated fat protects African green monkeys from coronary artery atherosclerosis, Arterioscler. Thromb. Vasc. Biol. 15, 2101-2110.
38. Rudel, L. L., Kelley, K., Sawyer, J. K., Shah, R., and Wilson, M. D. (1998) Dietary monounsaturated fatty acids promote aortic atherosclerosis in LDL receptor-null, human ApoB100-Over-expressing transgenic mice, Arterioscler. Thromb. Vasc. Biol. 18, 1818-1827.