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Stereoselective Synthesis of Stable Isotope Labeled L‐α‐Amino Acids: Synthesis of L−[4− 13 C] and L−[3,4− 13 C 2 ]Aspartic Acid
Author(s) -
Lodwig Siegfried N.,
Unkefer Clifford J.
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580310204
Subject(s) - chemistry , aspartic acid , serine , enantiomer , stereoselectivity , potassium cyanide , stereochemistry , hydrolysis , amino acid , cyanide , yield (engineering) , organic chemistry , catalysis , enzyme , biochemistry , materials science , metallurgy
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.