Acetic Acid → 6-[2-Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid

Participants

Reaction Conditions

Reaction Steps

Structure 8b was prepared according to the method described by F. Hayase et al., J. Biol. Chem 263: 3758-64 (1989). The procedure was approximately as follows: ε-(2-Formyl-5-hydroxymethyl-pyrrol-1-yl)-caproic Acid (Caproyl Pyrraline or structure 8b) was synthesized for use as a hapten. D-Glucose (18 g) and ε-amino caproic acid (13.1 g) were dissolved in distilled water (20 mL), and the pH was adjusted to 4.0 with acetic acid. The solution was refluxed at 100° C. for 3 h. The resulting brown solution was extracted with ethyl acetate, dried with anhydrous sodium sulfate, and concentrated. The concentrate was charged onto a silica gel column for flash chromatography in 3:1 hexane/ethyl acetate. 2,4-Dinitrophenylhydrazine-positive fractions containing caproyl pyrraline were collected and recrystallized from ether/hexane. The yield was 1 g. Proton NMR: (CDCl3) δ 1.33-1.92 (m, 6H, 3×CH2), 2.39 (t 2H, CH2), 4.33 (t, 2H, CH2), 4.72 (s, 2H, CH2OH), 6.23 (d, 1H, pyrrole-4H), 6.99 (d, 1H, pyrrole-3H), 9.46 (s, 1H, CHO). IR 3500, 2950-2860 (br), 1725, 1645, and 1400 cm-1. UVmax 297 nm (H2O) (ε=1.61×104 mol-1 liter cm-2). Chemical ionization mass spectrometry-millimass: C12H17O4N as theoretical ion distribution, M1 =239 1158. Mass spectrometry analysis was performed with a HP 5985A mass spectrometer Crlewlett-Packard). Chemical ionization mass spectrometry was analyzed with methane as the reaction gas. NMR, IR, and UV properties were identical with those of synthetic neopentyl and L-lysyl pyrraline.

Provenance & Evidence