Synthesis of the sugar moiety of TIME-EA4, a glycopeptide isolated from silkworm diapause eggs |
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Authors: | Hiro Shouji Usuki Yoshinosuke Iio Hideo |
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Affiliation: | Department of Material Science, Graduate School of Science, Osaka City University, Japan. |
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Abstract: | We describe the efficient synthesis of the tetrasaccharide, 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1-->6)-2,4-di-O-acetyl-3-O-allyl-beta-D-mannopyranosyl-(1-->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl-(1-->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl azide, which is the protected form of the sugar unit of TIME-EA4 that is isolated from the diapausing eggs of the silkworm, Bombyx mori. The beta-linked D-mannoside of the tetrasaccharide was obtained using the conventional oxidation-reduction method for inversion of the configuration at the C-2 hydroxyl group of beta-D-glucoside. The reduction was effected with NaBH(4) in a methanolic solution in a ratio of 98:2 in favor of the beta-D-mannoside that was obtained in 87% yield. |
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Keywords: | TIME-EA4 N-Glycan Glycosylation d-Mannoside" target="_blank">β-d-Mannoside Oxidation-reduction |
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