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.
Highlights
Peptidoglycan (PGN) is an essential component of the cell walls of virtually all bacteria
In connection with our interest in the synthesis of DAP [8], we report on a new synthesis of orthogonally protected meso-DAP and applications to preparing N-acyl iE-DAP from protected iE-DAP (Figure 1)
Because DAP-containing peptides such as iE-DAP and FK565 [9,10] have significant biological activities and functions, the synthesis of orthogonally protected meso-DAP as synthetic intermediates has been a subject of considerable interest by several groups [11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26]
Summary
Peptidoglycan (PGN) is an essential component of the cell walls of virtually all bacteria. The function of the PGN is to preserve cell integrity by withstanding the internal osmotic pressure [1,2]. PGN can function as a potent immunostimulator and an adjuvant for antibody production. 2 (NOD1 and NOD2) that mediate host recognition of bacterial molecules [4,5,6]. The recognition core of Nod stimulatory molecules is γ-D-glutamyl-meso-diaminopimelic acid (iE-DAP) which is a constituent of most Gram-negative and some Gram-positive bacteria. Synthetic, lipophilic, N-acyl iE-DAP derivatives have been shown to be potent NOD 1 agonists [7]. Molecules 2013, 18 peptides would be expected to function as NOD 1 agonists. In connection with our interest in the synthesis of DAP [8], we report on a new synthesis of orthogonally protected meso-DAP and applications to preparing N-acyl iE-DAP from protected iE-DAP (Figure 1)
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