Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters: Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine

K. M. Patel; L. A. Sklar; R. Currie; Henry J. Pownall; J. D. Morrisett; J. T. Sparrow

doi:10.1007/BF02533521

Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters: Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine

K. M. Patel, L. A. Sklar, R. Currie, Henry J. Pownall, J. D. Morrisett, J. T. Sparrow

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Abstract

A rapid, high yield method for the preparation of cholesteryl esters is described. The method is a modification of the catalytic procedure previously applied to the acylation of sn-glycero-3-phosphoryl-choline (Patel, K.M., J.D. Morrisett, and J.T. Sparrow, J. Lipid Res., 20:676 (1979). Cholesteryl esters are formed in excellent yield by acylating cholesterol with fatty acid anhydride or fatty acid and dicyclohexylcarbodiimide in methylene chloride containing 4-pyrrolidinopyridine. The versatility of the method is demonstrated by the preparation of the cholesteryl esters of saturated, unsaturated, spinlabeled, and labile fluorescent fatty acids.

Original language	English (US)
Pages (from-to)	816-818
Number of pages	3
Journal	Lipids
Volume	14
Issue number	9
DOIs	https://doi.org/10.1007/BF02533521
State	Published - Sep 1979

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Cell Biology

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10.1007/BF02533521

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title = "Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters: Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine",

abstract = "A rapid, high yield method for the preparation of cholesteryl esters is described. The method is a modification of the catalytic procedure previously applied to the acylation of sn-glycero-3-phosphoryl-choline (Patel, K.M., J.D. Morrisett, and J.T. Sparrow, J. Lipid Res., 20:676 (1979). Cholesteryl esters are formed in excellent yield by acylating cholesterol with fatty acid anhydride or fatty acid and dicyclohexylcarbodiimide in methylene chloride containing 4-pyrrolidinopyridine. The versatility of the method is demonstrated by the preparation of the cholesteryl esters of saturated, unsaturated, spinlabeled, and labile fluorescent fatty acids.",

author = "Patel, {K. M.} and Sklar, {L. A.} and R. Currie and Pownall, {Henry J.} and Morrisett, {J. D.} and Sparrow, {J. T.}",

year = "1979",

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doi = "10.1007/BF02533521",

language = "English (US)",

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T1 - Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters

T2 - Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine

AU - Patel, K. M.

AU - Sklar, L. A.

AU - Currie, R.

AU - Pownall, Henry J.

AU - Morrisett, J. D.

AU - Sparrow, J. T.

PY - 1979/9

Y1 - 1979/9

N2 - A rapid, high yield method for the preparation of cholesteryl esters is described. The method is a modification of the catalytic procedure previously applied to the acylation of sn-glycero-3-phosphoryl-choline (Patel, K.M., J.D. Morrisett, and J.T. Sparrow, J. Lipid Res., 20:676 (1979). Cholesteryl esters are formed in excellent yield by acylating cholesterol with fatty acid anhydride or fatty acid and dicyclohexylcarbodiimide in methylene chloride containing 4-pyrrolidinopyridine. The versatility of the method is demonstrated by the preparation of the cholesteryl esters of saturated, unsaturated, spinlabeled, and labile fluorescent fatty acids.

AB - A rapid, high yield method for the preparation of cholesteryl esters is described. The method is a modification of the catalytic procedure previously applied to the acylation of sn-glycero-3-phosphoryl-choline (Patel, K.M., J.D. Morrisett, and J.T. Sparrow, J. Lipid Res., 20:676 (1979). Cholesteryl esters are formed in excellent yield by acylating cholesterol with fatty acid anhydride or fatty acid and dicyclohexylcarbodiimide in methylene chloride containing 4-pyrrolidinopyridine. The versatility of the method is demonstrated by the preparation of the cholesteryl esters of saturated, unsaturated, spinlabeled, and labile fluorescent fatty acids.

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Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters: Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine

Abstract

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