Total synthesis of FK-156 isolated from a Streptomyces as an immunostimulating peptide: application of a novel copper chelate amino protection

The first ferrocene analogues of muramyldipeptide

“…Herein, we report MDP analogues which contain Fca instead of iGln. Having in mind that activity of previously described MDP analogues depends on their structure and stereochemistry, [13][14][15][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] we decided to prepare MDP analogues consisting of Lor D-Ala incorporated between muramic acid and Fca. For this purpose, Boc-Fca-OMe (1) was deprotected by action of gaseous HCl in EtOAc and the obtained hydrochloride salt was treated with excess of NEt 3 .…”

Peptidoglycan as Nod1 ligand; fragment structures in the environment, chemical synthesis, and their innate immunostimulation

“…77 The DAP containing peptide, FK-156 (lactyl L-Ala-g-D-Glu-meso-DAP-Gly), was found and synthesized as an immunostimulatory component of Streptomyces olivaceogriseus by the Fujisawa Pharma group. 78,79 During the same period, lauroyl tetrapeptide (L-Ala-g-D-Glu-LL-DAP-D-Ala) was also found to be immunostimulatory. 80 Based on these seed molecules, a series of DAP-containing peptides were synthesized, and their immunostimulatory activities were examined.…”

Structural characteristics of peptidoglycan fragments required to prime mice for induction of anaphylactoid reactions by lipopolysaccharides

“…Murine macrophages digested bacterial peptidoglycans and released peptidoglycan fragments including disaccharide-dipeptide (6,21). The lactyl peptide used in this study is a synthetic compound mimicking a natural compound that was isolated from the fermentation broths of Streptomyces olivaceogriseus and Streptomyces violaceus (4,5). Therefore, the muramyl and lactyl peptides possessing the above immunobiological activities were possibly produced by bacteria in vivo.…”