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

Yukako Saitoemail, Yuichi Yoshimuraemail, Hideaki Wakamatsuemail and Hiroki Takahata* email
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)
PDF Full-text Download PDF Full-Text [269 KB, Updated Version, uploaded 23 January 2013 09:50 CET]
The original version is still available [292 KB, uploaded 16 January 2013 11:58 CET]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert