TY - JOUR
T1 - From methylglyoxal to new immunopotentiating ascorbic acid derivatives
AU - Fodor, G.
AU - Sussangkarn, K.
AU - Arnold, R.
AU - Mathelier, H.
AU - Mohacsi, T.
AU - Mujumdar, R.
AU - Butterick, J.
AU - Veltri, R. W.
PY - 1987/12/1
Y1 - 1987/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0023578438&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0023578438&partnerID=8YFLogxK
M3 - Article
C2 - 3118623
AN - SCOPUS:0023578438
SN - 0237-6261
VL - 22
SP - 165
EP - 179
JO - Acta Biochimica et Biophysica Hungarica
JF - Acta Biochimica et Biophysica Hungarica
IS - 2-3
ER -