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Molecules 2013, 18(1), 1162-1173; doi:10.3390/molecules18011162
Article

A Facile Synthesis of Fully Protected meso-Diaminopimelic Acid (DAP) and Its Application to the Preparation of Lipophilic N-Acyl iE-DAP

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Received: 5 December 2012 / Revised: 8 January 2013 / Accepted: 9 January 2013 / Published: 16 January 2013
(This article belongs to the Special Issue Chemical Protein and Peptide Synthesis)
Download PDF [269 KB, 18 June 2014; original version 18 June 2014]

Abstract

Synthesis of beneficial protected meso-DAP 9 by cross metathesis of the Garner aldehyde-derived vinyl glycine 1b with protected allyl glycine 2 in the presence of Grubbs second-generation catalyst was performed. Preparation of lipophilic N-acyl iE-DAP as potent agonists of NOD 1-mediated immune response from 9 is described.
Keywords: protected meso-diaminopimelic acid; N-acyl iE-DAP; cross metathesis protected meso-diaminopimelic acid; N-acyl iE-DAP; cross metathesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Saito, Y.; Yoshimura, Y.; Wakamatsu, H.; Takahata, H. A Facile Synthesis of Fully Protected meso-Diaminopimelic Acid (DAP) and Its Application to the Preparation of Lipophilic N-Acyl iE-DAP. Molecules 2013, 18, 1162-1173.

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