From methylglyoxal to new immunopotentiating ascorbic acid derivatives

G. Fodor, K. Sussangkarn, R. Arnold, H. Mathelier, T. Mohacsi, R. Mujumdar, J. Butterick, R. W. Veltri

Research output: Contribution to journalArticlepeer-review

Abstract

In Szent-Gyorgyi's search for α-dicarbonyl compounds that play an important role in cell regulation, 3 desoxyglucosulose was isolated first from liver but did not prove active. Methylglyoxal came next, however, its toxicity prompted Szent-Gyorgyi to suggest a combination with ascorbic acid which, indeed led to immunopotentiating enediol acetals although of low stability. Therefore the vinylogue of methylglyoxal, acetylacrolein was coupled with L-ascorbic acid carbanion. This second new reaction, of the aldol-type, led to the stable, potent immunoactive compound, 2-(5-methylfuryl)-3-ketogulonolactone cyclohemiketal that forms a completely surprising H-bond with succinic anhydride and succinimide based on an X-ray study. A third new reaction in which ascorbic acid plays the role of a Michael donor to α,β-unsaturated aldehydes and ketones proved now to be of general validity; it is unexpectedly acid catalyzed and the adducts formed with aliphatic and alicyclic olefin ketones have definite immunopotentiating effect. A brief description of the biological effects of all types of new compounds is outlined.

Original languageEnglish (US)
Pages (from-to)165-179
Number of pages15
JournalActa Biochimica et Biophysica Hungarica
Volume22
Issue number2-3
StatePublished - Dec 1 1987

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry

Fingerprint Dive into the research topics of 'From methylglyoxal to new immunopotentiating ascorbic acid derivatives'. Together they form a unique fingerprint.

Cite this