Next Article in Journal
Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one
Next Article in Special Issue
Case Studies of the Synthesis of Bioactive Cyclodepsipeptide Natural Products
Previous Article in Journal
Bioassay-Guided Isolation of DPP-4 Inhibitory Fractions from Extracts of Submerged Cultured of Inonotus obliquus
Previous Article in Special Issue
Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles
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

,
,
 and
*
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 / 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]
SciFeed

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 (CC BY 3.0).

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert