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
Article Menu

Article Versions

Export Article

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

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 / 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 (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & 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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

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