Structural Determination of Three Glycoasparagines Isolated from the Urine of a Patient with Aspartylglycosaminuria

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Abstract
Three different glycoasparagines were isolated from the urine of a patient with aspartylglycosaminuria and their structures determined using sugar, amino acid and methylation analysis, enzymic degradation and measurements of the optical rotations. The structures were 2-acetamido-1-N-(4''-L-aspartyl)-2-deoxy-.beta.-D-glucopyranosylamine (yield 135 mg/l), .beta.-D-galactopyranosyl-(1 .fwdarw. 4)-2-acetamido-1-N-(4''-L-aspartyl)-2-deoxy-.beta.-D-glucopyranosylamine (yield 35 mg/l) and .alpha.-D-mannopyranosyl-(1 .fwdarw. 6)-.beta.-D-mannopyranosyl-(1 .fwdarw. 4)-2-acetamido-2-deoxy-.beta.-D-glucopyranosyl-(1 .fwdarw. 4)-2-acetamido-1-N-(4''-L-aspartyl)-2-deoxy-.beta.-D-glucopyranosylamine (yield 30 mg/l). The 1st 2 compounds have previously been described, whereas the 3rd compound is different from any of the glycoasparagines isolated before.