Abstract
Two reports have appeared on the isolation of 4-methylproline from natural sources. Hulme and Arthington1 isolated an amino-acid from apples, and tentatively assigned the structure of 4-methylproline to it as a result of elemental analysis, colour tests and chromatographic similarity to synthetic material. Later, two of us reported that hydrolysis of a peptide antibiotic yielded, inter alia, an amino-acid with the same chromatographic behaviour2. We have now been able to isolate 4-methylproline from perry (variety, Huffcap Seedling) by successive fractionation on ‘Dowex-2’ and ‘Dowex-50’ ion exchange resins. The crystalline amino-acid (8 mgm. from 5 litres of perry) has [α]D ca. − 52° (c., 0.3 in water), and is rigorously identified as trans-4-methyl-L-proline (I) by comparison with the optically active synthetic compound obtained as follows :
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References
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BURROUGHS, L., DALBY, S., KENNER, G. et al. Absolute Configuration of 4-Methylproline from Perry. Nature 189, 394–395 (1961). https://doi.org/10.1038/189394a0
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DOI: https://doi.org/10.1038/189394a0
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