Deuterated biogenic amine metabolites: Preparation of ring-deuterated 4-hydroxy-3-methoxymandelic acid

✍ Scribed by Kym F. Faull; Patricia J. Anderson; Jack D. Barchas

• Publisher: John Wiley and Sons
• Year: 1981
• Tongue: French
• Weight: 203 KB
• Volume: 18
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580180721

✦ Synopsis

mandelic a c i d (commonly r e f e r r e d t o as v a n i l l y l m a n d e l i c a c i d (VMA)) l a b e l l e d w i t h deuterium i n t h e methoxy group has been prepared b o t h e n z y m a t i c a l l y , from S-adenosyl-L-methionine-methyl-d3 and dihydroxymandelic a c i d u s i n g c a t e c h o l -0-methyl t r a n s f e r a s e ( 4 ) , and c h e m i c a l l y from c a t e c h o l , d e u t e r a t e d iodomethane, and g l y o x y l i c a c i d ( 6 ) . Ring-deuterated VMA can be prepared b y a hydrogend e u t e r i u m excnange r e a c t i o n under a c i d c o n d i t i o n s ( 2 ) , b u t because o f r a p i d

p o l y m e r i z a t i o n o f VMA under these c o n d i t i o n s , t h e y i e l d i s v e r y low and i t i s d i f f i c u l t t o p u r i f y t h e f i n a l p r o d u c t ( 5 ) . We w i s h t o r e p o r t t h a t i n one s t e p u s i n g t h e p l a t i n u m c a t a l y z e d r e a c t i o n between aromatic r i n g p r o t o n s and deuterium o x i d e ( 7 ) , we have been a b l e t o prepare, i n reasonable y i e l d , c r y s t a l l i n e r i n g -d e u t e r a t e d VMA s u i L a b l e f o r use as an i n t e r n a l s t a n d a r d i n S I M assays. 4-Hydroxy-3-methoxy-P l a t i n u m o x i d e (132 mg, 0.6 mmol) was suspendeo i n water (12 m l ) and, w i t h c a r e taken t o ensure t h a t t h e temperature d i d n o t go above 50°C, reduced b y t h e c a u t i o u s and s t e p w i s e a d d i t i o n o f sodium b o r o h y d r i d e (920 mg, 24 mmol).