A new reaction of o-benzoquinone with N-acetyl-DL-tryptophan (a 3-substituted indole) and characterisation of the product
Narasimhan, S.; Vithayathil, P.J.
Indian Journal of Biochemistry and Biophysics 23(4): 215-219
1986
ISSN/ISBN: 0301-1208 PMID: 3570339 Document Number: 272454
o-Benzoquinone reacts with 3-substituted indoles under acidic conditions to give products having distinct UV characteristics. The o-benzoquinone derivative of N-acetyl-DL-tryptophan prepared in the presence of HCl was chromatographically homogeneous and had one equivalent of chloride per mole. Potentiometric titration showed the presence of carboxyl and hydroxyl groups. Based on PMR, IR and elementary analysis a structure has been assigned to the derivative where the o-benzoquinone moiety is incorporated at the indole nitrogen of N-acetyl-DL-tryptophan.