A facile synthesis of fully protected meso-diaminopimelic acid (DAP) and its application to the preparation of lipophilic N-acyl iE-DAP

Yukako Saito; Yuichi Yoshimura; Hideaki Wakamatsu; Hiroki Takahata

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

Molecules. 2013 Jan 16;18(1):1162-73. doi: 10.3390/molecules18011162.

Authors

Yukako Saito¹, Yuichi Yoshimura, Hideaki Wakamatsu, Hiroki Takahata

Affiliation

¹ Laboratory of Organic and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Diaminopimelic Acid / analogs & derivatives*
Diaminopimelic Acid / chemical synthesis
Esterification
Hydrophobic and Hydrophilic Interactions
Nod1 Signaling Adaptor Protein / agonists
Oxidation-Reduction
Peptidoglycan / chemistry

Substances

Nod1 Signaling Adaptor Protein
Peptidoglycan
Diaminopimelic Acid
N(2)-(gamma-D-glutamyl)-meso-2,2'-diaminopimelic acid