Procedures f o r t h e p r e p a r a t i o n of N-feruloylglycine (11) , -DL-alanine ( X X ) , -DL-valine (XXII) and -G l e u c i n e ( X X I V ) by c l a s s i c a l methods a r e proposed and compared. The s p e c t r a l c h a r a c t e r i s t i c s and Rf-values of t h e s u b s t a n c e s a r e i n c l u d e d . The compounds were s y n t h e s i z e d because N-feruloylamino a c i d s were r e q u i r e d as t e s t s u b s t a m e s d u r i n g a n i n v e s t i g a t i o n i n connection w i t h t h e expected presence of N -f e r u l o y l p r o t e i n s i n b a r l e y [l, 2,3] .
Free f e r u l i c a c i d (4-hydroxy-3-methoxycinnamic a c i d ) ( I ) i s wide spread i n n a t u r e [4]. I n a d d i t i o n , t h e compoundo c c u r s a l s o i n bound form, and a b r i e f survey of t h e d i f f e r e n t t y p e s of l i n k a g e s i n which t h e component has s o f a r been i d e n t i f i e d , may be found i n a r e c e n t paper by V a n Sumere e t a1[3]. I n t h e same p u b l i c a t i o n , t h e i d e n t i f i c a t i o n of N-feruloylglycyl-L-phenylalanyl-R, as a n a t u r a l l y o c c u r r i n g sequence of b a r l e y p r o t e i n s , i s d e s c r i b e d . Because N-cinnamoyl-and N-(subs t i t u t e d cinnamoy1)-amino a c i d s and p e p t i d e s were needed as t e s t s u b s t a n c e s d u r i n g t h e i n v e s t i g a t i o n , t h e p r e p a r a t i o n of t h e s e compounds was s t u d i e d . Indeed, l i t t l e i n f o r m a t i o n on s u b s t a n c e s of t h i s group i s a v a i l a b l e i n t h e 1 i t e r a t u r e . B o o t h e t a1 [5] have s y n t h e s i z e d N-feruloylglycine (11) and N-m. coumaroylglycine (1111, while Armstrong e t a1 [6] and Acheson e t a1 [7] have i d e n t i f i e d I1 and N-p.coumaroylglycine ( I V ) i n u r i n e . pounds of t h i s group has n e v e r been d e s c r i b e d . I n t h i s first paper o f a s e r i e s , we t h e r e f o r e propose procedures f o r the s y n t h e s i s of N-feruloylglycine ( I T ) , -DL-alanine ( X X ) , -D G v a l i n e (XXII) and ->leucine ( X X I V ) .However, t o o u r knowledge, t h e p r e p a r a t i o n of o t h e r com--2 4 3 -