Folate analogues: 27. syntheses of 14carbon-labeled 10-deazaaminopterin and 10-ethyl-10-deazaaminopterin

✍ Scribed by M. M. Nair; Nitin T. Nanavati

• Book ID: 102375674
• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: French
• Weight: 286 KB
• Volume: 24
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580240803

✦ Synopsis

vevsi ty o f South A1 abama Mobile, AL 36688 SUMARY 10-Deazaaminopterin (1) and 10-Ethyl-10-deazaaminopterin ( 2 )

labeled uniformly w i t h 14C a t the glutamate moiety were prepared by the following procedure. Uniformly labeled L-glutamic acid was converted t o i t s dimethyl ester (3). -4-Amino-4-deoxy-10-deazapteroic a c i d ( 4)

and 4-amino-4-deoxy-10ethyl-10-deazapteroic acid (5) were converted t o t h e i r respective mixed anhydrides 6 and 7 w i t h isobutylchloroformate.

labeled dimethyl-L-gl utamate gave dimethyl-10-deazaaminopterin (

and dimethyl 10-ethyl-10-deazaaminopterin (9)respectively, which on m i l d a l k a l i n e hydrolysis gave the t a r g e t compounds -1 and -2 i n .~22-25% y i e l d , based on the amount of radiolabeled glutamic acid used.