Synthesis of 2-(5-hydroxymethyl-2-formylpyrrol-1-yl)propionic acid lactone

Abstract

propionic acid lactone was synthesized in six steps with a 17.0% overall yield, starting from L-alanine. The synthetic route involved the Clauson-Kaas reaction, Vilsmeier reaction, and transesterification. The transesterification was the key step in the formation of the target compound.

Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract

“…Also, their expected deprotonated molecules of m / z 281.1240 [M – H] − , 240.0511 [M – H] − , and 254.0668 [M – H] − were detected by means of LC–ESI-TOF-MS, and consequently the identification of the chemical structures was confirmed as α-[(2-formyl-5-hydroxymethyl)­pyrrol-1-yl]­arginine ( 3 ), α-[(2-formyl-5-hydroxymethyl)­pyrrol-1-yl]­aspartic acid ( 12 ), and α-[(2-formyl-5-hydroxymethyl) pyrrol-1-yl]­glutamic acid ( 19 ). So far, three analogues of glycine, alanine, and S -allyl- l -cysteine were reported in the literature; ,, herein, three new compounds of this structure type are described.…”

“…NMR spectroscopy and highresolution MS of the isolated compounds enabled the identification of the known compounds as 1,2,3-butanetriol,4,4′-(2,5-pyrazinediyl)bis-(1), 1,2,3-butanetriol,4,4′-(2,6pyrazinediyl)bis-( 2), DDMP (6), 1,2,3-butanetriol-4-(6methyl-2-pyrazinyl) (7), 5-hydroxymethyl-2-furan-carboxylic acid (8), hydroxymethylfurfural (9), thymidine (10), 5hydroxymethyl-1H-pyrrole-2-carbaldehyde ( 11), 2-formyl-5-(hydroxymethyl)-pyrrole-1-acetic acid ( 13), (2S)-1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylic acid (15), 5hydroxy-3,4-dimethyl-2(5H)-furanone ( 16), 5-hydroxymaltol (18), α-[(2-formyl-5-hydroxymethyl)pyrrol-1-yl]alanine (22), cordyrrole A (25), respectively. Although compounds 1, 2, 7, and 22 are literature known compounds, so far the identification was proposed only by mass spectrometry; 19,20,31 herein, their structure elucidation by means of NMR and TOF MS (ESI) data are presented for the first time (Supporting Information). The spectroscopic data for compounds 6, 8−11, 13, 15, 16, 18, and 25 were well in line with the literature data (Supporting Information).…”

“…32 Also, their expected deprotonated molecules of m/z 281.1240 [M − H] − , 240.0511 [M − H] − , and 254.0668 [M − H] − were detected by means of LC−ESI-TOF-MS, and consequently the identification of the chemical structures was confirmed as α-[(2-formyl-5hydroxymethyl)pyrrol-1-yl]arginine (3), α-[(2-formyl-5hydroxymethyl)pyrrol-1-yl]aspartic acid (12), and α-[(2formyl-5-hydroxymethyl) pyrrol-1-yl]glutamic acid(19). So far, three analogues of glycine, alanine, and S-allyl-L-cysteine were reported in the literature;20,29,32 herein, three new compounds of this structure type are described.Besides, in compound 14, a γ-butyrolactone moiety was identified based on the HMBC connectivities of H-8 → C-9,11; H-10 → C-9,11; and H-11 → C-8,9,10. Further interpretation of the HMBC spectrum clarified a C-8-N-1 linkage between the pyrrole and γ-butyrolactone moieties due to signals of H-8 → C-2,5.…”