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The synthesis of D-erythro- and D-threo-α-amino-β,γ-dihydroxy-n-butyric acids

Niemann, Carl and Nichols, Peter L., Jr. (1942) The synthesis of D-erythro- and D-threo-α-amino-β,γ-dihydroxy-n-butyric acids. Journal of Biological Chemistry, 143 (1). pp. 191-202. ISSN 0021-9258.

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We repeated the synthesis of Fischer and Feldmann [2] and obtained, as they did, the amino acid with [α]D24 = -13.7° in good yield. However, in addition another α-amino-β,γ-dihydroxy-n-butyric acid, with [α]D24 = 16.0°, was isolated from the reaction mixture. It is the purpose of this communication to show that the amino acid with [α]D24 = -13.7° is not a mixture of disastereoisomers, but is D-threo-α-amino-β,γ-dihydroxy-n-butyric acid, and that the amino acid with [α]D24 = 16.0° is D-erythro-α-amino-β,γ-dihydroxy-n-butyric acid.

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Additional Information:Copyright © 1942 by the American Society for Biochemistry and Molecular Biology. (Received for publication, December 8, 1941) We wish to thank Mr. Erik Heegaard for his assistance in connection with these experiments.
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Record Number:CaltechAUTHORS:NIEjbc42
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10995
Deposited By: Archive Administrator
Deposited On:22 Jun 2008
Last Modified:03 Oct 2019 00:14

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