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Molecules 2006, 11(7), 564-573; doi:10.3390/11070564
Article

Novel Furanoid α-Substitued α-Amino Acid as a Potent Turn Mimic in Peptide Synthesis

* ,
 and
Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, SK-040 01 Košice, Slovak Republic
* Author to whom correspondence should be addressed.
Received: 23 June 2006 / Revised: 20 July 2006 / Accepted: 21 July 2006 / Published: 26 July 2006
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Abstract

A stereoselective approach has been developed to the new sugar amino acid and potential potent turn mimic 5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O- isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose 3-C-carboxylic acid (12), via the [3,3]-sigmatropic rearrangement of allylic thiocyanates (Z)-6 and (E)-7, prepared from D-xylose. The synthesis of a new dipeptide 13 is also described.
Keywords: Sugar amino acids; stereoselectivity; sigmatropic rearrangement; carbohydrate-based mimetics; peptidomimetic; β-turn mimic Sugar amino acids; stereoselectivity; sigmatropic rearrangement; carbohydrate-based mimetics; peptidomimetic; β-turn mimic
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Martinková, M.; Gonda, J.; Raschmanová, J. Novel Furanoid α-Substitued α-Amino Acid as a Potent Turn Mimic in Peptide Synthesis. Molecules 2006, 11, 564-573.

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