Side reactions in the preparation of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Autor:	Patricia Verheyden, Koen Iterbeke, Georges Laus, Dirk Tourwé
Rok vydání:	1998
Předmět:	chemistry.chemical_compound chemistry organic chemicals Dimer Pharmacology toxicology Carboline-3-carboxylic acid Formaldehyde Tryptophan Organic chemistry heterocyclic compounds Methylene Biochemistry Two-dimensional nuclear magnetic resonance spectroscopy
Zdroj:	Letters in Peptide Science. 5:121-123
ISSN:	1573-496X 0929-5666
Popis:	During a study on the preparation of the conformationally restricted analogue of tryptophan into 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 1 by a Pictet–Spengler condensation with formaldehyde, two side products were detected: N-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 2 and a dimer 3 of two 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid units linked by a methylene group. Their structures were determined by HPLC-MS and 2D NMR spectroscopy. By changing the isolation procedure, the N-hydroxymethyl compound was removed. Treatment of the mixture with TFA in water converted the dimer into 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 1.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8bd216f9116d6386d1d6b42afa57b8b2 https://doi.org/10.1007/bf02443452 Zobrazit plný text záznamu Full text from SpringerLink