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Versatile and stereoselective synthesis of alpha and gamma-unsaturated amino acids by wittig reaction

Reference

04704-01

Patents status

French priority patent application FR1159112 filed on October 10th, 2011 and entitled « Synthèse versatile et stéréospécifique d’acides aminés gamma, delta-insaturés par la réaction de Wittig »

Inventors

Sylvain JUGE
Jérôme BAYARDON
Emmanuelle REMOND
Marie-Joëlle ONDEL-EYMIN

commercial status

Exclusive or non-exclusive licenses

Laboratory

Description

CONTEXT

a-amino acids present an important biological interest, because they constitute peptides and proteins. As they play an important role in the organism, the chemist seeks to synthesize structural analogous, in order to obtain new biological properties or modified peptides.
Among different strategies to develop analogous of natural amino acids, it is possible to introduce an unsaturation on the lateral chain. The unsaturation may be more or less distant from the alpha carbon. However, synthesis known in the prior art to obtain unsaturated amino acids are not adapted to the synthesis of libraries of compounds: either they are compound-specific, or involve multiple steps, or are not stereoselective, or have unsatisfying yields and more generally lack of versatility. There remains a need for the development of new methods of synthesis of libraries of unsaturated a-amino acids, and especially of g,d-unsaturated amino acids.

TECHNICAL DESCRIPTION

In the present work, the inventors have developped a process for the stereoselective synthesis of g,d-unsaturated amino acids performed by Wittig reaction using a phosphonium salt in presence of weak base in suitable solvent, and under phase transfert conditions.

The two filed patents applications protect the phosphonium reagent and the g,d-unsaturated amino acids, the process for synthesizing these compounds, and also the intermediates involved in the synthesis.

DEVELOPMENT STAGES

  • Building blocks for the synthesis of library of unsaturated or functionnalized amino acids
  • Suitable process for multi-gram scale: synthesis up to multigrams

BENEFITS

The present process clearly surpasses previous proposed methods for obtaining unsaturated amino acids. Indeed, it is versatile, stereoselective, presents high yields while leading to novel aminoacids.

INDUSTRIAL APPLICATIONS

Two applications are targetted in the present invention. First of all, the present phosphonium salts can be used as new reagents for unsaturated amino acids synthesis. Second of all, said amino acids can be used as intermediates for peptide synthesis or other molecule synthesis or directly as a biologically active compound.

Publication: Stereoselective Synthesis of Unsaturated and Functionalized L-NHBoc aminoacids, using Wittig Reaction under Mild Phase-Transfer Conditions, J. Org. Chem. 2012, 77, 7579-7587.

For further information, please contact us (Ref 04704-01)

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