The synthesis of antigenic glycopeptides,2-acetamido-N-(.BETA.-L-aspartyl)-2-deoxy-4-O-.BETA.-(D-galactopyranosyl)-.BETA.-D-glucopyranosylamine. (N-Acetyllactosaminyl-L-asparagine).

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概要

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• The title compound, serving as intermediate in the chemical and biochemical synthesis of glycopeptides and as a reference substance in the structure elucidation of glycoproteins, was synthesized. 2-Acetamido-4-<I>O</I>-allyl-3,6-di-<I>O</I>-benzyl-2-deoxy-β-D-glucopyranosyl azide was reduced to the corresponding β-D-glucosylamine and coupled with 1-benzyl <I>N</I>-benzyloxycarbonyl-L-aspartate to give 2-acetamido-4-<I>O</I>-allyl-3,6-di-<I>O</I>-benzyl-<I>N</I>-[(<I>S</I>)-3-benzyloxycarbonyl-3-benzyloxycarbonylamino)propionyl]-2-deoxy-β-D-glucopyranosylamine. Removal of the allyl group of the latter followed by condensation with 2,3,4,6-tetra-<I>O</I>-acetyl-α-D-galactopyranosyl bromide gave the fully protected <I>N</I>-acetyllactosaminyl-L-asparagine. De-blocking of the <I>O</I>-acetyl, benzyl, and benzyloxycarbonyl groups gave the title compound.

• 公益社団法人 日本化学会の論文

著者

• Jeanloz Roger

  Laboratory For Carbohydrate Research Departments Of Biological Chemistry And Medicine Harvard Medica

• Jeanloz Roger

  Laboratory for Carbohydrate Research, Department of Biological Chemistry and Medicine, Harvard Medical School and Massachusetts General Hospital

• Shaban Mohammed

  Department of Chemistry, Faculty of Science, Alexandria University

関連論文

• Studies on Solanum tuberosum Agglutinin
• The synthesis of antigenic glycopeptides,2-acetamido-N-(.BETA.-L-aspartyl)-2-deoxy-4-O-.BETA.-(D-galactopyranosyl)-.BETA.-D-glucopyranosylamine. (N-Acetyllactosaminyl-L-asparagine).

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