ISSN:
1573-3904
Keywords:
Pictet–Spengler condensation
;
restricted amino acids
;
tryptophan
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1008813617005
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