Total synthesis of an antigenic heptasaccharide motif found in the cell-wall lipooligosaccharide of Mycobacterium gordonae strain 989

Abstract

An antigenic heptasaccharide motif of the cell-wall glycolipid of Mycobacterium gordonae strain 989 has been synthesized in a linear fashion by using a general glycosylation condition and minimum number of protecting group manipulation. All suitably protected monosaccharide intermediates were prepared from commercially available reducing sugars following some novel methodologies recently developed in our laboratory. Most of the synthetic intermediates were obtained as solid compounds in excellent yields.

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

“…The target tetrasaccharide as its p -methoxyphenyl (PMP) glycoside was synthesized following a sequential glycosylation approach from the suitably functionalized monosaccharide intermediates 2 [13], 3 [14], 4 [15] and 5 [16]. These monosaccharide intermediates were prepared from the commercially available reducing sugars by using a number of recently developed reaction conditions (Fig.…”

Concise Synthesis of a Hexasaccharide Related to the Adhesin Receptor of Streptococcus oralis ATCC 55229

“…1). Starting from L-rhamnose, compounds 4 [14] and 5 [15] were prepared using similar reaction conditions reported earlier.…”

Concise synthesis of a heptasaccharide antigen found in the cell-wall lipopolysaccharide of Mycobacterium gordonae strain 990

“…Several differentially protected monosaccharide derivatives (Fig. 3), prepared from commercially available sugars using reported methodologies [23] have been used to construct the target molecule 1.…”

“…Compounds 2 and 3 were coupled together stereoselectively to furnish disaccharide derivative 9, which was transformed into the disaccharide acceptor 10 following an earlier reported reaction conditions [23]. N-Iodosuccinimide (NIS)-trimethylsilyl trifluoromethanesulfonate (TMSOTf) [25,26] mediated β-selective glycosylation of disaccharide derivative 10 with thioglycoside 3 afforded trisaccharide derivative 11 in 80% yield, which was benzylated to furnish trisaccharide derivative 12 under a one-pot deacetylationbenzylation protocol reported earlier [27].…”