Synthesis of [4‐ 11 C]amino acids via ring‐opening of aziridine‐2‐carboxylates | Zendy

Gillings N. M. | Zendy; Gee A. D. | Zendy

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Synthesis of [4‐ 11 C]amino acids via ring‐opening of aziridine‐2‐carboxylates

Author(s) -

Gillings N. M.,

Gee A. D.

Publication year - 2001

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.517

Subject(s) - chemistry , aziridine , yield (engineering) , hydrolysis , isopropyl , cyanide , butyric acid , aspartic acid , ring (chemistry) , carboxylate , amino acid , medicinal chemistry , stereochemistry , nuclear chemistry , organic chemistry , biochemistry , materials science , metallurgy

Ring‐opening of N ‐( tert ‐butoxycarbonyl)aziridine‐2‐isopropyl carboxylate with no‐carrier‐added (n.c.a.) [ 11 C]cyanide is reported. Following purification by HPLC, the protected D , L ‐[4‐ 11 C] β ‐cyanoalanine was subsequently hydrolysed, to yield D , L ‐[4‐ 11 C]asparagine or D , L ‐[4‐ 11 C]aspartic acid, or reduced followed by hydrolysis to give D , L ‐2,4‐diamino[4‐ 11 C]butyric acid. Typical syntheses starting with 10 GBq hydrogen [ 11 C]cyanide yielded 1–1.4 GBq of [4‐ 11 C]amino acid within 30 min, giving the labelled amino acids in 30–40% decay corrected radiochemical yield (counted from [ 11 C]cyanide) with radiochemical purities of 95%, 98% and 60%, respectively. Copyright © 2001 John Wiley & Sons, Ltd.

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