Synthesis and conformational analysis of polydepsipeptides

✍ Scribed by Goodman, Murray ;Becktel, Wayne ;Katakai, Ryoichi ;Wouters, Guy

• Publisher: Wiley (John Wiley & Sons)
• Year: 1981
• Weight: 655 KB
• Volume: 4
• Category: Article
• ISSN: 0025-116X
• DOI: 10.1002/macp.1981.020041981108

✦ Synopsis

SYNTHESIS AND CONFORMATIONAL ANALYSIS OF POLYDEPSIPEPTIDES Murray Goodman, Wayne B e c k t e l , R y o i c h i Katakai*, and Guy Wouters Department o f Chemistry, U n i v e r s i t y o f C a l i f o r n i a , San Diego, La J o l l a , C a l i f o r n i a 92093, USA A b s t r a c t -The s y n t h e s i s and c o n f o r m a t i o n a l a n a l y s i s o f s e v e r a l p o l yd e p s i p e p t i d e s c o n t a i n i n g a l k y l o r p o l a r r e s i d u e s a r e r e p o r t e d . F i v e separate r o u t e s t o t h e s y n t h e s i s o f d e p s i p e p t i d e monomers and two methods o f p o l y m e r i z a t i o n a r e d e s c r i b e d . t a i n i n g a l a n i n e . v a l i n e , l e u c i n e , l a c t i c a c i d , a -h y d r o x y i s o v a l e r i c a c i d , g l u t a m i c a c i d , and l y s i n e were prepared and t h e i r conformations i n s o l u t i o n analyzed. H e l i x -t o -c o i l t r a n s i t i o n s f o r s p e c i f i c p o l yd e p s i p e p t i d e s a r e observed i n s i n g l e o r g a n i c s o l v e n t s such as c h l o r o f o r m , t e t r a h y d r o f u r a n , o r t r i f l u o r o e t h a n o l . A s t a t i s t i c a l thermodynamic t h e o r y o f polymer m e l t i n g s u c c e s s f u l l y d e s c r i b e s t h e observed t r a n s i t i o n s and a l l o w s q u a n t i t a t i v e d e t e r m i n a t i o n o f t h e tendency o f s p e c i f i c amino a c i d r e s i d u e s t o form h e l i c a l a r r a y s .