The Facile Synthesis of a Series of Tryptophan Derivatives

Blaser, G.; Sanderson, J.M.; Batsanov, A.S.; Howard, J.A.K.

Abstract

This study reports a facile method for the synthesis of a variety of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions provides some insights into the likely mechanism of the reaction.

Citation

Blaser, G., Sanderson, J., Batsanov, A., & Howard, J. (2008). The Facile Synthesis of a Series of Tryptophan Derivatives. Tetrahedron Letters, 49(17), 2795-2798. https://doi.org/10.1016/j.tetlet.2008.02.120

• Journal Article Type: Article
• Publication Date: Apr 1, 2008
• Deposit Date: Jun 21, 2011
• Publicly Available Date: Jan 3, 2012
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Not Peer Reviewed
• Volume: 49
• Issue: 17
• Pages: 2795-2798
• DOI: https://doi.org/10.1016/j.tetlet.2008.02.120
• Public URL: https://durham-repository.worktribe.com/output/1562336