Collect. Czech. Chem. Commun. 1990, 55, 1326-1335

Synthesis of tetrasaccharide containing glycopeptides related to bacterial cell wall starting from free tetrasaccharide by the pentafluorophenyl ester method

Jan Ježeka, Evgenii A. Makarovb, Tamara A. Balashovab, Miloš Buděšínskýa, Tatyana M. Andronovab and Vadim T. Ivanovb

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Shemyakin Institute of Bioorganic Chemistry, U.S.S.R. Academy of Sciences, 117871 GSP Moscow, V-437 U.S.S.R.


The free tetrasaccharide GlcNAc-MurNAc-GlcNAc-MurNAc was converted into the tetrasaccharide bis-pentafluorophenyl ester I by treatment with bis(pentafluorophenyl)carbonate. Reaction of I with suitably protected peptides afforded [GlcNAc-MurNAc-L-Ala-D-Glu(OBzl)2]2 (II) and [GlcNAc-MurNAc-L-Ala-D-iGln-L-Lys(Z)-OBzl]2 (IV). Catalytic hydrogenolysis of compound II and IV yielded (GlcNAc-MurNAc-L-Ala-D-Glu)2 (III) and (GlcNAc-MurNAc-L-Ala-D-iGln-L-Lys)2 (V), respectively. [GlcNAc-MurNAc-L-Ala-D-iGln-L-Lys(St)2]2 (VI) was prepared from compound V by reaction with stearic acid N-hydroxysuccinimide ester.