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Synthesis of 4-Methylene-DL-proline: a Naturally Occurring Racemic Amino-acid

Abstract

ROTATIONAL and other data from the synthesis of an optically active derivative1 have shown that 4-methylene-proline (I) isolated under non-epimerizing conditions from loquat seeds2 is racemic. The suspected biogenetic precursor, γ-methyleneglutamic acid, on the other hand, has been found only in optically active form3, although in different plant sources4. In view of the rare occurrence of racemic amino-acids in Nature we wish to record the following simple synthesis of 4-methylene-DL-proline, along with direct comparison evidence confirming its identity with the natural compound.

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References

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BURGSTAHLER, A., TROLLOPE, M. & AIMAN, C. Synthesis of 4-Methylene-DL-proline: a Naturally Occurring Racemic Amino-acid. Nature 202, 388–389 (1964). https://doi.org/10.1038/202388b0

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