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The transformation of ascorbigens in acidic media; structure of ascorbigen B
A.M. Korolev, E. I. Lazhko, I. V. Yartseva, I. L. Plikhtyak, L. G. Aleksandrova, B. V. Rosynov, M. N. Preobrazhenskaya
Institute of New Antibiotics, Academy of Medical Sciences of the USSR, Moscow; All-Union Cancer Research Centre, Academy of Medical Sciences of the USSR, Moscow; M. M. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: The transformation of ascorbigens upon heating at pH<7 proceeds by an intermolecular mechanism involving release of L-ascorbic acid and addition of an (indol-3-yl)methyl moiety to another molecule of ascorbigen (Ia) to yield 1'-[(indol-3"-yl)methyl] as-corbigen (IIa), 2'-[(indol-3"-yl)methyl] ascorbigen (IIIa) and 2'-{[2"-[indol-3′′′-yl)methyl]indol-3"-yl]methyl} ascorbigen (IVa). Similar transformations were performed for 5'-bromascorbigen. 1′-Methyl-2'-[(l′′-methylindol-3′′-yl)methyl]ascorbigen and 1'-butyl-2'-[(l′′-butylindol-3′′-yl)methyl]ascorbigen were obtained from 1'-methylascorbigen and 1'-butylascorbigen; ascorbigen B is identified as a mixture of (IIa). (IIIa) and (IVa), 2'-[(indol-3′′-yl)methyl]ascorbigen (IIIa) being predominant.
Russian Journal of Bioorganic Chemistry 1991, 17 (7):981-987