[Synthesis of lipophilic muramoyldipeptide derivatives].
beta-Glycosides of N-acetylglucosamine, obtained by the oxazoline synthesis, with 2-dodecyltetradecanol-1 and 2,3-didodecyloxypropanol-1 as aglycons, were converted into muramic acids and then coupled with the dipeptide to give lipophilic glycosides of muramoyldipeptide. On the other hand, condensation of 2-dodecyltetradecanyl esters of glycine and 6-aminohexanoic acid with Boc-L-Ala-D-Glu-NH2 gave the corresponding lipophilic tripeptides, which upon coupling with alpha-benzyl-4,6-O-benzylyden-N-acetylmuramic acid yielded lipophilic esters of muramoyltripeptides. The protecting groups were removed by acid hydrolysis and hydrogenolysis.
Kur'ianov
V O
VO
Zemliakov
A E
AE
Chirva
V Ia
VIa
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D006868:Hydrolysis; D050356:Lipid Metabolism; D011487:Protein Conformation
D000119:Acetylmuramyl-Alanyl-Isoglutamine
Sintez lipofil'nykh proizvodnykh muramoildipeptida.