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Enantioselective synthesis and antioxidant activity of 3‐(3,4‐dihydroxyphenyl)‐glyceric acid—Basic monomeric moiety of a biologically active polyether from Symphytum asperum and S. caucasicum
Author(s) -
Merlani Maia,
Barbakadze Vakhtang,
Amiranashvili Lela,
Gogilashvili Lali,
Yannakopoulou Elina,
Papadopoulos Kyriakos,
Chankvetadze Bezhan
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20823
Subject(s) - chemistry , glyceric acid , enantiomer , caffeic acid , enantioselective synthesis , organic chemistry , chlorogenic acid , stereochemistry , sharpless asymmetric dihydroxylation , moiety , quinic acid , alkylation , antioxidant , catalysis , chromatography
The racemic and enantioselective synthesis of a novel glyceric acid derivative, namely, 2,3‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐propionic acid as well as the antioxidant activities is described. The virtually pure enantiomers, (+)‐(2 R ,3 S )‐2,3‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐propionic acid and (−)‐(2 S ,3 R )‐2,3‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐propionic acid were synthesized for the first time via Sharpless asymmetric dihydroxylation of trans‐caffeic acid derivatives using the enantiocomplementary catalysts, (DHQD) 2 ‐PHAL and (DHQ) 2 ‐PHAL. The determination of enantiomeric purity of the novel chiral glyceric acid derivatives was performed by high‐performance liquid chromatographic techniques on the stage of their alkylated precursors. The novel glyceric acid derivatives show strong antioxidant activity against hypochlorite and N , N ‐diphenyl‐ N ‐picryl‐hydrazyl free radical. Their antioxidant activity is about 40‐fold higher than that of the corresponding natural polyether and three‐fold higher of trans‐caffeic acid itself. Chirality, 2010. © 2010 Wiley‐Liss, Inc.