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Configurational Notation of the Tartaric Acids

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Abstract

IN an abstract of a paper describing a method of preparation of (−)-tartaric acid from D-xylose the acid is named L(−)-tartaric acid1. As this seemed odd, a number of standard text-books were consulted; these were about equally divided in naming dextro-rotatory tartaric acid D(+) or L(+). This confusion arises because the relationship of the tartaric acids to the reference compound D(+)-glycer-aldehyde has been established in two different ways, from which opposite conclusions have been drawn:

(+)-Tartaric acid is related to D(+)-glyceraldehyde by the series of reactions2: (+)-tartaric acid → (+)-malic acid → (+)-isoserine → (−)-glyceric acid → (+)-glyceraldehyde: hence D(+)-tartaric acid. (−)-Tartaric acid is obtained by oxidation of D-threose, which is related in configuration to D(+)-glyceraldehyde: hence D(−)-tartaric acid.

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References

  1. Brit. Chem. Abst., A, ii, 198 (1950).

  2. Ber., 47, 2027 (1914).

  3. J. Biol. Chem., 91, 71 (1931).

  4. J. Chem. Soc., 410 (1935).

  5. Nature, 166, 178 (1950).

  6. Brit. Chem. Abst., A, ii, 93 (1950).

  7. J. Chem. Soc., 2687 (1950).

  8. J. Chem. Soc., 612 (1951).

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BUCHANAN, C. Configurational Notation of the Tartaric Acids. Nature 167, 689–690 (1951). https://doi.org/10.1038/167689a0

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