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

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 resp...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-01, Vol.18 (1), p.1162-1173
Main Authors: Saito, Yukako, Yoshimura, Yuichi, Wakamatsu, Hideaki, Takahata, Hiroki
Format: Article
Language:English
Subjects:
Acids
Alcohol
Catalysis
cross metathesis
Diaminopimelic Acid - analogs & derivatives
Diaminopimelic Acid - chemical synthesis
Esterification
Gram-positive bacteria
Hydrophobic and Hydrophilic Interactions
N-acyl iE-DAP
Nod1 Signaling Adaptor Protein - agonists
Oxidation-Reduction
Peptides
Peptidoglycan - chemistry
Pharmaceuticals
protected meso-diaminopimelic acid
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules18011162