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Synthesis of (2S,4S)-[5-13C] leucine, (2R,4S)-[5-13C] leucine, and (2RS)-[1,2-13C2] leucine

✍ Scribed by D. John Aberhart; Bruce H. Weiller

Publisher: John Wiley and Sons
Year: 1983
Tongue: French
Weight: 256 KB
Volume: 20
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580200512

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✦ Synopsis

SYNTHESIS OF (2s , 4S)-[5-l 3C] LEUC INE , (2R ,4S)-[5-' 3C] LEUC I NE , AND (2RS)-[1 ,2-13C,] LEUCINE D. John Aberhart* and Bruce H. W e i l l e r The Worcester Foundation f o r Experimental B i o l o g y Shrewsbury, Massachusetts 01545 SUMMARY (2RSY3S)-[4-13 ClVal i n e was d i a z o t i z e d and converted t o (2RS,3j~-[4-13C1-2-bromoi s o v a l e r i c a c i d , which on r e d u c t i o n w h Zn/HC1 gave (3S)-[4-C l i s o v a l e r i c acid. T h i s was converted t o (3S)-[4-igy3 isovaleraldehyde, which was converted by a S t r e c k e r s y n t h e s i s t o (2RSy4S)-[5-$J leucine. Resolu on v i a t h e Nwas s i m i l a r l y f p v e r t e d t o [l-a c e t a t e t h e n gave (2S,4S) and {$Ry4S)-[5-C] leucines. [l-!j C ] I s o v a l e r i c a c i d t h e s i s u s i n g K CN, gave (2RS)-[1,2-79 C21 l e u c i n e .

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