title: A facile synthesis of fully protected meso-diaminopimelic acid (DAP) and its application to the preparation of lipophilic N-acyl iE-DAP.
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.
authors: Laboratory of Organic and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors: Yukako
authors: Y
authors: Saito
authors: Yuichi
authors: Y
authors: Yoshimura
authors: Hideaki
authors: H
authors: Wakamatsu
authors: Hiroki
authors: H
authors: Takahata
mesh_terms: D002384:Catalysis; D003960:Diaminopimelic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004951:Esterification; D057927:Hydrophobic and Hydrophilic Interactions; D053474:Nod1 Signaling Adaptor Protein / Q000819:agonists; D010084:Oxidation-Reduction; D010457:Peptidoglycan / Q000737:chemistry
chemical_list: D053474:Nod1 Signaling Adaptor Protein; D010457:Peptidoglycan; D003960:Diaminopimelic Acid; C034331:N(2)-(gamma-D-glutamyl)-meso-2,2'-diaminopimelic acid