The Facile Synthesis of a Series of Tryptophan Derivatives

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

doi:10.1016/j.tetlet.2008.02.120

The Facile Synthesis of a Series of Tryptophan Derivatives

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

Authors

G. Blaser

Dr John Sanderson j.m.sanderson@durham.ac.uk
Associate Professor

A.S. Batsanov

J.A.K. Howard

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Peer Reviewed	Not Peer Reviewed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