P-42 meso-ジアミノピメリン酸類の新規合成法の開発と生理活性ペプチド合成への応用(ポスター発表の部)

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2,6-Diaminopimelic acid (DAP) is a naturally occurring amino acid found in both bacteria and higher plants. meso-DAP and (S,S)-DAP serve as the precursors in the biosynthesis of L-lysine in both bacteria and higher plants. meso-DAP is also an essential component of the peptidoglycan of most pathogenic bacteria. A number of peptidoglycan fragments featuring the DAP residue exhibit various biological activites such as antitumor, immunostimulant and sleep-inducing activities. FK-565 (1), DAP-containing structure, enhances host defense ability against microbial infections and exhibits strong antiviral activity and remarkable antitumor potency. iE-DAP is a peptidoglycan (PGN)-specific dipeptide and stimulates Nodl, which is a member of family of intracellular proteins that mediate host recognition of bacterial peptidoglycan. N-Acyl iE-DAP 2 and 3 exhibit higher ability to stimulate Nodl than the original iE-DAP. We describe a convenient synthesis of orthogonally protected meso-DAP and 1 using cis-1,4-diacetoxycyclohept-2-ene (4). We developed the new method to synthesize protected meso-DAP 20 using Grubbs' cross metathesis between vinyl 16 and allylglycine derivative 17. This strategy has been applied to total synthesis of 2 and 3.
天然有機化合物討論会の論文
2008-09-01