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Lipidic Peptides, IX. Synthesis and Structural Elucidation of Lipophilic Azidothymidine Conjugates
Author(s) -
Hussain Rohanah,
Toth Istvan,
Gibbons William A.
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920131
Subject(s) - chemistry , conjugate , alkyl , amino acid , molecule , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , mathematical analysis , mathematics
Azidothymidine (AZT) esters of lipidic amino acid and oligomers, together with AZT‐5′‐lipidic sulphide were synthesised. The AZT conjugates with ester linkages ( 3a – e ) were prepared by coupling the lipidic amino acids and their oligomers to the 5′‐hydroxyl terminus of AZT. The sulphide conjugate 5 was synthesised by treating AZT‐5′‐tosylate ( 4 ) with octadecanethiol. In order to examine the effect of different lipophilicities on the activity of the AZT molecule conjugates, the lipidic amino acid units were varied from 1 to 3 and the length of the alkyl chain from 9 to 17 carbon atoms.