• Journal Article

Chemical synthesis and structural elucidation of a new serotonin metabolite: (4R)-2-[(5 '-hydroxy-1 ' H-indol-3 '-yl)-methyl]thiazolidine-4-carboxylic acid

Citation

Jin, C., Burgess, J., Gopinathan, M., & Brine, G. (2006). Chemical synthesis and structural elucidation of a new serotonin metabolite: (4R)-2-[(5 '-hydroxy-1 ' H-indol-3 '-yl)-methyl]thiazolidine-4-carboxylic acid. Tetrahedron Letters, 47(6), 943-946. DOI: 10.1016/j.tetlet.2005.11.153

Abstract

A new serotonin (5-hydroxytryptamine) metabolite, (4R)-2-[(5?-hydroxy-1?H-indol-3?-yl)methyl]thiazolidine-4-carboxylic acid (5?-HITCA), was synthesized in 30% overall yield. The key step involved oxidation of protected 5-hydroxytryptophol using IBX followed by spontaneous cyclization with l-cysteine. The stereochemistry of condensation product thiazolidine-4-carboxylic acid was studied using NMR spectroscopy techniques.