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The facile synthesis of a series of tryptophan derivatives.

Blaser, G. and Sanderson, J. M. and Batsanov, A. S. and Howard, J. A. K. (2008) 'The facile synthesis of a series of tryptophan derivatives.', Tetrahedron letters., 49 (17). pp. 2795-2798.


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.

Item Type:Article
Full text:(SMUR) Submitted Manuscript Under Review
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Status:Not peer-reviewed
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Record Created:21 Jun 2011 15:05
Last Modified:03 Jan 2012 14:22

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