Synthesis of LeX and LeY Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups |
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Authors: | Santiago Figueroa Pérez Raul González Lio Violeta Fernández Santana Vicente Verez Bencomo |
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Institution: | Laboratory of Synthetic Antigens, Facultad de Química , Universidad de La Habana , Ciudad Habana , CUBA , 10400 |
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Abstract: | Abstract 5-Azido-3-oxa-l-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide β-D-Gal-(1→4)-α-L-Fuc-(1→3)]-GlcNAc and the tetrasaccharide α-L-Fuc-α-(1→2)-β-D-Gal-(1→4)-α-L-Fuc-(1→3)]-GlcNAc that represent the epitopes defining the human blood groups Lex and Ley. The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency. |
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