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Structural analysis of oxidation products of urofuran acid by hypochlorous acid
Author(s) -
Ohki Toyokazu,
Maeda Kenji,
Sakakibara Jinsaku,
Suzuki Eiji,
Yamanaka Naoki
Publication year - 1993
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536357
Subject(s) - hypochlorous acid , chemistry , hemiacetal , nucleophile , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , stereochemistry , catalysis
The oxidation of urofuran acid derivatives (1–2) by hypochlorous acid (HOCl) was investigated with the goal to possibly simplify the detection of their metabolites in biological materials. The oxidation products of 3‐carboxy‐4‐methyl‐5‐propyl‐2‐furanpropionic acid (1) were obtained as an isomeric mixture and confirmed to exist as cis (3a) and trans (3b) isomers, based on their 13 C nuclear magnetic resonance (NMR) spectra. Similarly, the products of 5‐H substituted acid 2 obtained by oxidation with HOCl were identified as 4a and 4b by 13 C and 1 H NMR which indicated the presence of cis and trans hemiacetal hydrogens at C‐5 in a ratio of 2.11∶1. The oxidation was found to proceed in a manner different from that of the F‐acid, because of the presence of the electron withdrawing COOCH 3 group at C‐3 which favored the nucleophilic attack on the carbonyl group to afford cis ‐ and trans ‐2,5‐dihydroxy‐2,5‐dihydrofurans (3a−b, 4a−b).