Reductones participate in redox reactions during amine-catalyzed sugar degradation

Glomb, Marcus A.; Pfahler, Christoph; Hiller, Rebekka L.

doi:10.1016/s0531-5131(02)00964-0

Cited by 2 publications

(1 citation statement)

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“…It also occurs in the alga Laurencia spectabilis (35) and is, therefore, named laurencione. The formation of 1,4-dideoxyosones has been explained by the dehydration of 1-deoxyketose obtained either by the reduction of 1-deoxyosone, for example, via Strecker degradation, or by its disproportionation (32,36). It can be also formed from oligosaccharides by a so-called "peeling off" mechanism (37).…”

Section: Resultsmentioning

confidence: 99%

Formation of Aroma Compounds from Ribose and Cysteine during the Maillard Reaction

Cerny

Davídek

2003

J. Agric. Food Chem.

111

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The headspace volatiles produced from a phosphate-buffered solution (pH 5) of cysteine and a 1 + 1 mixture of ribose and [(13)C(5)]ribose, heated at 95 degrees C for 4 h, were examined by headspace SPME in combination with GC-MS. MS data indicated that fragmentation of ribose did not play a significant role in the formation of the sulfur aroma compounds 2-methyl-3-furanthiol, 2-furfurylthiol, and 3-mercapto-2-pentanone in which the carbon skeleton of ribose remained intact. The methylfuran moiety of 2-methyl-3-(methylthio)furan originated from ribose, whereas the methylthio carbon atoms came partly from ribose and partly from cysteine. In 3-mercapto-2-butanone one carbon unit was split from the ribose chain. On the other hand, all carbon atoms in 3-thiophenethiol stemmed from cysteine. In another trial cysteine, 4-hydroxy-5-methyl-3(2H)-furanone and [(13)C(5)]ribose were reacted under the same conditions. The resulting 2-methyl-3-furanthiol was mainly (13)C(5)-labeled, suggesting that it stems from ribose and that 4-hydroxy-5-methyl-3(2H)-furanone is unimportant as an intermediate. Whereas 2-mercapto-3-pentanone was found unlabeled and hence originated from 4-hydroxy-5-methyl-3(2H)-furanone, its isomer 3-mercapto-2-pentanone was formed from both 4-hydroxy-5-methyl-3(2H)-furanone and ribose. A new reaction pathway from ribose via its 1,4-dideoxyosone is proposed, which explains both the formation of 2-methyl-3-furanthiol without 4-hydroxy-5-methyl-3(2H)-furanone as an intermediate and a new way to form 3-mercapto-2-pentanone.

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