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

Laboratory of Organic and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan
* Author to whom correspondence should be addressed.
Received: 5 December 2012; in revised form: 8 January 2013 / Accepted: 9 January 2013 / Published: 16 January 2013
(This article belongs to the Special Issue Chemical Protein and Peptide Synthesis)
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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

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MDPI and ACS Style

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.

AMA Style

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(1):1162-1173.

Chicago/Turabian Style

Saito, Yukako; Yoshimura, Yuichi; Wakamatsu, Hideaki; Takahata, Hiroki. 2013. "A Facile Synthesis of Fully Protected meso-Diaminopimelic Acid (DAP) and Its Application to the Preparation of Lipophilic N-Acyl iE-DAP." Molecules 18, no. 1: 1162-1173.

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