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Stereoselective Synthesis of Stable Isotope Labeled L-α-Amino Acids: Synthesis of L−[4−13C] and L−[3,4−13C2]Aspartic Acid

✍ Scribed by Siegfried N. Lodwig; Clifford J. Unkefer

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
542 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

We have developed a stereoselective route to isotopically labeled L‐aspartic acid using L‐serine as a chiral precursor. Labeled serine, prepared biosynthetically was N‐protected by conversion to the N‐t‐Boc derivative. (N‐t‐Boc)‐[3−^13^C]Serine is cyclized to its β‐lactone which was treated with potassium [^13^C]cyanide to yield L‐β‐[3,4−^13^C~2~]cyanoalanine. Hydrolysis of the cyanoalanine yielded L‐[3,4−^13^C~2~]aspartic acid. Similarly, L‐[4−^13^C]aspartate was produced from L‐serine and K^13^CN. Using this route, the L‐enantiomer was produced in 96% excess.

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