Collect. Czech. Chem. Commun. 1980, 45, 606-610

Synthesis of conjugates of 5'-O-carboxymethyl-5-halogeno-2'-deoxyuridines and 5'-O-carboxymethyl-5-halogenouridines with proteins

Helmut Pischela, Antonín Holýb and Günther Wagnera

a Sektion Biowissenschaften-Pharmazie, Karl-Marx-Universitat, Leipzig, G.D.R.
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia


5'-O-Carboxymethyl-2'-deoxyuridine (Ia), its 5-fluoro, 5-bromo and 5-iodo derivatives Ib-Id, and 5'-O-carboxymethyluridine (IIa) and its 5-halogeno derivatives IIb-IId, on reaction with isobutyl chloroformate and tri-n-butylamine afforded mixed anhydrides IIIa-IIId and IVa-IVd. Condensation of III and IV with human serum albumin or bovine gamma-globulin at pH 8.0 gave conjugates Va-Vd to VIIIa-VIIId, the yield of the covalently bound haptene being 28 to 43%.