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Aminoacid and protein conjugates with biologically active purines
Author(s) -
VidalGomez J.,
Greenbaum J. H.,
GinerSorolla A.
Publication year - 1975
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570120212
Subject(s) - chemistry , purine metabolism , purine , conjugate , bovine serum albumin , purine analogue , yield (engineering) , biochemistry , enzyme , mathematical analysis , materials science , mathematics , metallurgy
Condensation products of amino acids and proteins with biologically active purines have been obtained to study their potential tumor inhibitory activity and as models for the preparation of conjugates with tumor specific antibodies. Among the new compounds are 2‐glycinyl‐6‐methylmercaptopurine ( 5 ), 2‐glycinyl‐6‐mercaptopurine ( 6 ), 2‐glycinyl‐6‐chloropurine ( 16 ), 2‐glycinyl‐6‐hydroxylaminopurine ( 18 ), 2‐glycinylpurine ( 8 ) and 2‐glycinyl‐6‐methylpurine ( 7 ). 9‐Alkylpurines led to new purine derivatives, such as 6‐chloro‐9 H ‐purine‐9‐acetic acid (22) and 6‐hydroxylamino‐9 H ‐purine‐9‐acetylhydroxamic acid ( 23 ). These derivatives were coupled to bovine serum albumin (BSA) to yield conjugates. The amino acid‐purines 6‐cysteinyl ( 27 ) and 6‐glutathionyl‐S‐purine 3‐oxide ( 28 ) were obtained from 6‐chloropurine 3‐oxide ( 26 ). Other protein‐purine 3‐oxide conjugates were obtained with 6‐mercaptopurine 3‐oxide ( 29 ) and 6‐bromomethylpurine 3‐oxide ( 33 ).