Abstract
LINKO and I1 isolated, last autumn, from Polygonatum officinale (and also from Convallaria majalis), a new imino-acid which on acid hydrolysis gave mostly homoserine. The elementary composition of the new compound corresponded to the formula (C4H7O2N)n and had [α]20D − 118.4° (in water). The compound had all its carboxyl groups free and contained no primary but only secondary amino-groups. Because the compound contained no double bonds, it must have a cyclic structure. A 4-membered ring containing an imino-group and a free carboxyl group linked to the ring could have satisfied the formula, but using the method of Wendt2 a molecular weight of approximately 300 was found, which is three times as high as that calculated for the simple molecule (six determinations in concentrations of 0.63–2.22 per cent in a non-polar solvent, the lactam of 4-amino-cyclo-hexane-carboxylic acid; calculated for (C4H7O2N)3, 303.3). On the basis of the molecular weight found, the compound seemed not to contain a simple 4-membered ring, even if all other known facts suggested this structure, but a corresponding ring three times as large and with three imino-groups in a ring to which three free carboxyl groups were linked. There was no other possibility of explaining the high molecular weight.
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References
Virtanen, A. I., and Linko, P., Acta Chem. Scand., 9, 551 (1955).
Wendt, G., Ber., 75, 425 (1942).
Fowden, L., Nature, 176, 347 (1955).
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VIRTANEN, A. A New Imino-Acid in some Liliaceae. Nature 176, 984 (1955). https://doi.org/10.1038/176984a0
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DOI: https://doi.org/10.1038/176984a0
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