Block synthesis of blood group tetrasaccharides B (types 1, 3 and 4)

Synthesis of ABO histo-blood group type I and II antigens

“…9 This strategy would enable an expedited synthesis of all three of the type I and II antigens in sufficient quantities for a range of investigations. A block synthesis, such as that reported by Bovin and co-workers, 17 would not enable access to the H structures. We chose to employ a 7-octen-1-yl aglycone for two reasons.…”

“…The chemical synthesis of all three type I antigens has been reported by Paulsen and Kolář 16 as well as by Bovin and co-workers. 17,18 The chemoenzymatic synthesis of the A type I and II tetrasaccharides was reported by Palcic and co-workers, 19 and more recently Wang and co-workers have developed a chemoenzymatic synthesis of the B type I antigen. 20 Interestingly, the latter study did not use the human glycosyltransferases, but rather three enzymes present in Escherichia coli O86, which produces a B type III mimetic in its lipopolysaccharide O-chain.…”

A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens

“…A mixture of 15 (372 mg, 329 µmol) and 16 (234 mg, 988 µmol), and NIS (148 mg, 658 µmol) was exposed to high vacuum for 1 h. The mixture was dissolved in CH 2 Cl 2 (13.2 mL), to which 4 Å molecular sieves (1.32 g) was added at rt. After stirring for 30 (18). To a solution of 17 (289 mg, 215 µmol) in AcOH/(CH 2 Cl) 2 (3:1, 14.3 mL) was added Zn powder (2.89 g) at rt.…”

“…We envisioned that chemically synthesized pure samples would enable a range of studies on the physiological and pathological implications of ABO group antigens. The chemical synthesis of type 1 glycans has been reported by several groups [4,[17][18][19][20][21][22][23], but reports on the synthesis of type 2 glycans have been limited [4,[24][25][26]. Also, it should be noted that synthetic studies of ABO antigens were first reported by Lemieux's group and they then focused on Lewis antigens [27][28][29][30][31].…”

Synthesis and NMR studies on the ABO histo-blood group antigens: synthesis of type III and IV structures and NMR characterization of type I–VI antigens

“…Although the synthesis of the ABO histo-blood group antigens by either chemical and chemoenzymatic approaches has been the subject of a number of investigations, the vast majority of attention has focused on the type I and II subtypes. [15][16][17][18][19] In contrast, much less work has focussed on the important type III and IV structures. In 1990, Bovin and Khorlin reported the synthesis of the A type III antigen.…”