TY - JOUR
T1 - Preparation of Deuterated Arachidonic Acid
AU - Taber, Douglass F.
AU - Phillips, Mark A.
AU - Hubbard, Walter C.
N1 - Funding Information:
This investigation was supported by the National Institutes of Health grant GM 15431. We acknowledge support from Biomedical Research Support Grant RR-05424 for MS and NMR instrumentation. We thank Dr. James Hamilton of Hoffmann La Roche for a generous gift of ETYA.
Funding Information:
The work described in this chapter was supported in part by U.S. Public Health Service NIH Contract N-01 HV82930 and NIH Grants AM 20387 and AM 18844.
PY - 1982/1/1
Y1 - 1982/1/1
N2 - It is reported preparation of [2H8]arachidonic acid from the precursor tetraacetylene eicosatetraynoic procedures gave rise to substantial double-bond isomerization and isotopic scrambling, leading to mixtures that yielded after purification only small quantities of the desired product. This chapter presents new preparation of deuterated arachidonic acid. For preparation of [2H8]arachidonate, round-bottom flask is charged with methyl [2H8]arachidonate, dimethoxyethane, and LiOH. The mixture is flushed with N2, then stirred at 60 ° under an N2 atmosphere. The reaction mixture was diluted with aqueous hydrochloric acid and extracted with CH2Cl2. The organic extracts were combined, dried over Na2SO4, filtered, and concentrated under vaccuum. The residue is taken up in methanol and chromatographed on a Waters μBondapak. Fractions are collected, and an aliquot of each was counted. The arachidonic acid usually appeared in fractions 52-64, with 95% recovery of applied radioactivity.
AB - It is reported preparation of [2H8]arachidonic acid from the precursor tetraacetylene eicosatetraynoic procedures gave rise to substantial double-bond isomerization and isotopic scrambling, leading to mixtures that yielded after purification only small quantities of the desired product. This chapter presents new preparation of deuterated arachidonic acid. For preparation of [2H8]arachidonate, round-bottom flask is charged with methyl [2H8]arachidonate, dimethoxyethane, and LiOH. The mixture is flushed with N2, then stirred at 60 ° under an N2 atmosphere. The reaction mixture was diluted with aqueous hydrochloric acid and extracted with CH2Cl2. The organic extracts were combined, dried over Na2SO4, filtered, and concentrated under vaccuum. The residue is taken up in methanol and chromatographed on a Waters μBondapak. Fractions are collected, and an aliquot of each was counted. The arachidonic acid usually appeared in fractions 52-64, with 95% recovery of applied radioactivity.
UR - http://www.scopus.com/inward/record.url?scp=13144250392&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=13144250392&partnerID=8YFLogxK
U2 - 10.1016/0076-6879(82)86207-1
DO - 10.1016/0076-6879(82)86207-1
M3 - Article
AN - SCOPUS:13144250392
SN - 0076-6879
VL - 86
SP - 366
EP - 369
JO - Methods in enzymology
JF - Methods in enzymology
IS - C
ER -