The acridinium ester 4-(2-succinimidyloxycarbonylethyl)phenyl-10-methylacridinium 9-carboxylate trifluoromethane sulfonate (AE), which reacts rapidly with alkaline hydrogen peroxide to produce light, has been used as a detection label in a number of assay procedures, including nucleic acid probe-based systems [Nelson et al. (1995) in Nonisotopic Probing, Blotting and Sequencing (Kricka, L. J., Ed.) pp 391-428, Academic Press, Inc., San Diego, CA]. We have synthesized a number of derivatives of this AE and characterized their chemiluminescent properties. These derivatives display significant differences in the kinetics of the chemiluminescence reaction as well as optimal pH for light production. These differences allow two or more derivatives to be simultaneously detected and quantitated in a single reaction vessel. Several of these derivatives have been covalently linked to nucleic acid probe molecules and have been further characterized in regard to chemiluminescence properties as well as hydrolysis of the ester bond in both single- and double-stranded conformations. On the basis of these properties, homogeneous assay formats utilizing DNA probes labeled with various AE derivatives were developed. Simultaneous detection and quantitation of Chlamydia trachomatis and Neisseria gonorrhoeae, the gag and pol regions of HIV, and wild-type and mutant HIV sequences was achieved with high sensitivity and discrimination.

The synthesis of racemic 6'0-hydroxyaristeromycin ( 8) is described. 7-tert-Butoxynorbomadiene (9) was oxidized to the corresponding cis-exo diol 10. Compound 10 was acetylated to give diacetate 11. Isopropylidenation gave ketal 12. Oxidation of diacetate 11 afforded dicarboxylic acid 13 which was converted into monoamide 14. Esterification with CH2N2 led to amide ester 15. Similarly, ketal 12 was oxidized to diacid 16 which was transformed to monoamide 18 via anhydride 17. Esterification afforded amide ester 19. Alternatively, diacid 16 was converted to monoester 20 which was then transformed to amide 19 by a mixed anhydride method. Hofmann rearrangement

We have prepared the nucleoamino acids 1-(3'-amino,3'-carboxypropyl)uracil (3) and 9-(3'-amino,3'-carboxypropyl)adenine (4) as (L)-enantiomers and as racemic mixtures. When 3 or 4 is suspended in water and treated with N,N'-carbonyldiimidazole, peptides are formed in good yield. The products formed from the (L)-enantiomers are hydrolyzed to the monomeric amino acids by pronase. Attempts to improve the efficiency of these oligomerizations by including a polyuridylate template in the reaction mixture were not successful. Similarly, oligomers derived from the (L)-enantiomer of 3 did not act as templates to facilitate the oligomerization of 4.

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