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

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

27 Scopus citations

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

Access to Document

10.1007/BF02533521

Cite this

@article{80dddb83c6d1461f93163fd69d2d24f5,

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",

month = sep,

doi = "10.1007/BF02533521",

language = "English (US)",

volume = "14",

pages = "816--818",

journal = "Lipids",

issn = "0024-4201",

publisher = "Springer Verlag",

number = "9",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0018713650&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0018713650&partnerID=8YFLogxK

U2 - 10.1007/BF02533521

DO - 10.1007/BF02533521

M3 - Article

AN - SCOPUS:0018713650

VL - 14

SP - 816

EP - 818

JO - Lipids

JF - Lipids

SN - 0024-4201

IS - 9

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this