TY - JOUR
T1 - Full Library of (Bis–allyl)-deuterated Arachidonic Acids
T2 - Synthesis and Analytical Verification
AU - Fomich, Maksim A.
AU - Bekish, Andrei V.
AU - Vidovic, Dragoslav
AU - Lamberson, Connor R.
AU - Lysenko, Ivan L.
AU - Lawrence, Peter
AU - Brenna, J. Thomas
AU - Sharko, Olga L.
AU - Shmanai, Vadim V.
AU - Shchepinov, Mikhail S.
PY - 2016/1/1
Y1 - 2016/1/1
N2 - Deuteration at bis-allylic positions slows down hydrogen abstraction, thereby reducing the rate of polyunsaturated fatty acids (PUFA) oxidation. Arachidonic acid undergoes oxidation through both enzymatic and non-enzymatic mechanisms, giving rise to a range of important products with variable biological activity, including pro- and anti-inflammatory properties. We report on the synthesis and verification of a full library of arachidonic acids variably deuterated at the bis-allylic (C7, C10, C13) positions: 7,7-D2-arachidonic acid, 10,10-D2-arachidonic acid, 13,13-D2-arachidonic acid, 7,7,10,10-D4-arachidonic acid, 7,7,13,13-D4-arachidonic acid, 10,10,13,13-D4-arachidonic acid, and 7,7,10,10,13,13-D6-arachidonic acid isotopologues. The library is intended to be useful for determining the relative importance of enzymatic versus non-enzymatic oxidation at particular sites in vivo.
AB - Deuteration at bis-allylic positions slows down hydrogen abstraction, thereby reducing the rate of polyunsaturated fatty acids (PUFA) oxidation. Arachidonic acid undergoes oxidation through both enzymatic and non-enzymatic mechanisms, giving rise to a range of important products with variable biological activity, including pro- and anti-inflammatory properties. We report on the synthesis and verification of a full library of arachidonic acids variably deuterated at the bis-allylic (C7, C10, C13) positions: 7,7-D2-arachidonic acid, 10,10-D2-arachidonic acid, 13,13-D2-arachidonic acid, 7,7,10,10-D4-arachidonic acid, 7,7,13,13-D4-arachidonic acid, 10,10,13,13-D4-arachidonic acid, and 7,7,10,10,13,13-D6-arachidonic acid isotopologues. The library is intended to be useful for determining the relative importance of enzymatic versus non-enzymatic oxidation at particular sites in vivo.
KW - fatty acids
KW - isotope effects
KW - lipids
KW - mass spectrometry
KW - NMR spectroscopy
UR - http://www.scopus.com/inward/record.url?scp=85038431598&partnerID=8YFLogxK
U2 - 10.1002/slct.201600955
DO - 10.1002/slct.201600955
M3 - Article
AN - SCOPUS:85038431598
SN - 2365-6549
VL - 1
SP - 4758
EP - 4764
JO - ChemistrySelect
JF - ChemistrySelect
IS - 15
ER -