Enzymatic preparation of an immunostimulant, the disaccharide-dipeptide, N-acetyl-beta-D-glucosaminyl-(1----4)-N-acetylmuramyl-L-alanyl-D-is ogl utamine, from a bacterial peptidoglycan.
The disaccharide-dipeptide N-acetyl-beta-D-glucosaminyl-(1----4)-N-acetylmuramyl-L-alanyl-D-isog lut amine has been obtained by an enzymatic degradation of the peptidoglycan of Actinomadura R39. The peptidoglycan was hydrolyzed successively by the three following enzymes: lysozyme, DD-carboxypeptidase from Streptomyces albus G and gamma-D-glutamyl-meso-diaminopimelate endopeptidase I from Bacillus sphaericus 9602. The by-products of the last reaction were eliminated by successive ion-exchange and gel-permeation chromatographies. Both chemical analysis and mass spectrometry show that the resulting disaccharide-dipeptide is a pure compound.
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000302:isolation & purification; D000192:Actinomycetales / Q000032:analysis; D000276:Adjuvants, Immunologic / Q000096:biosynthesis; D002473:Cell Wall / Q000032:analysis; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D010450:Endopeptidases / Q000378:metabolism; D009113:Muramidase / Q000378:metabolism; D002267:Muramoylpentapeptide Carboxypeptidase / Q000378:metabolism; D010457:Peptidoglycan / Q000378:metabolism*
D000276:Adjuvants, Immunologic; D010457:Peptidoglycan; D000119:Acetylmuramyl-Alanyl-Isoglutamine; C023868:N-acetyl-beta-glucosaminyl-N-acetylmuramyl-alanylisoglutamine; D009113:Muramidase; D010450:Endopeptidases; D002267:Muramoylpentapeptide Carboxypeptidase; C019404:gamma-D-glutamyl-meso-diaminopimelate peptidase I