Synthesis of 5-aminopentyl 4,6-O-[(R)-1-carboxyethylidene]-β-d-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein

Concise synthesis of the pentasaccharide O-antigen of Escherichia coli O83:K24:H31 present in the Colinfant vaccine

“…Removal of the benzoyl group from compound 15 followed by protection with tert-butyldiphenylsilyl group afforded trisaccharide derivative 16, which on removal of benzylidene acetal using HClO 4 -SiO 2 furnished trisaccharide diol acceptor 17 (Scheme 2). Selective glycosylation of the trisaccharide acceptor 17 with disaccharide thioglycoside donor 8 in the presence of NIS-TfOH [24,26] furnished pentasaccharide derivative 18 in 76% yield. Presence of signals at δ [102.9 (C-1 E ), 102.8 (C-1 A ), 100.2 (C-1 B ), 98.6 (C-1 D ), 97.0 (C-1 C )] in the 13 C NMR spectra confirmed the formation of required pentasaccharide derivative 18.…”

“…Glycosylation of 4-methoxyphenyl 2,3,4-tri-O-benzyl-β-Dgalactopyranoside (2) [23] with the thioglycoside donor 3 [24] in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) [25,26] gave disaccharide derivative 9 in 91% yield. Formation of compound 9 was confirmed from its spectral data [δ 5.47 (s, PhCH), 4.90 (d, J=8.5 Hz, H-1 B ), 4.69 (d, J=7.5 Hz, H-1 A ) in 1 H NMR and at δ 103.7 (C-1 A ), 101.9 (C-1 B ), 101.4 (PhCH) in 13 C NMR spectra].…”

Synthesis of oligosaccharide fragments corresponding to the exopolysaccharide released by Streptococcus macedonicus Sc 136

“…Removal of the benzylidene acetal [30] from the compound 15 using HClO 4 -SiO 2 afforded tetrasaccharide diol 16 in 90% yield (Scheme 1). Selective glycosylation of tetrasaccharide diol acceptor 16 with ethyl thioglycoside donor 8 [22], prepared from D-glucose in five steps, in the presence of NISTMSOTf [25] furnished pentasaccharide derivative 17 in 78% yield. Conventional acetylation followed by removal of benzylidene acetal [30] from the compound 17 using HClO 4 -SiO 2 afforded pentasaccharide acceptor 18 in 95% yield, which was selectively glycosylated with ethyl thioglycoside donor 9 [23], prepared from D-galactose, in the presence of NIS-TMSOTf [25] to give hexasaccharide derivative 19 in 81% yield.…”

“…2) from suitably functionalized mono-and disaccharide intermediates are presented in Schemes 1, 2, 3, 4 and 5. Compounds 4-10 [18][19][20][21][22][23][24] were synthesized following earlier literature reports (Fig. 3).…”

Separation Media in Affinity Chromatography of Proteins - A Critical Review

“…Ziegler and others (Ziegler et al, 1994) synthesized 5-aminopentyl 4,6-O-[(R)-1-carboxyethylidene]-β-D-galactopyranoside and coupled this ligand to epoxypropyl-modified polyacrylamide beads. This stationary phase was used for the affinity chromatography of human serum amyloid P (SAP) protein.…”