Synthesis of a hapten to be used in development of immunoassays for trans-3'-hydroxycotinine, a major metabolite of cotinine.

Abstract:

:4-Carboxyl-substituted analogues of trans-3'-hydroxycotinine were synthesized to be covalently linked to macromolecules for antibody production. 3-Pyridyl-N-methylnitrone was condensed with dimethyl fumarate to give two isomeric isoxazolidines. Hydrogenolysis of the major product [2RS-(2 alpha,3 alpha,3 beta)]-3-carbomethoxy-3- [[(benzyloxy)carbonyl]oxy]-1-methyl-5-oxo-2-(3-pyridinyl)pyrrolidine with Pd/C followed by hydrolysis gave [2RS-(2 alpha,3 beta,4 beta)]-4-hydroxy-1-methyl-5-oxo-2-(3-pyridinyl)-3- pyrrolidinecarboxylic acid. The same compound was also prepared in two steps in high yield starting with dibenzyl fumarate and 3-pyridyl-N-methylnitrone.

journal_name

Chem Res Toxicol

authors

Desai DH,Amin S

doi

10.1021/tx00023a006

subject

Has Abstract

pub_date

1991-09-01 00:00:00

pages

524-7

issue

5

eissn

0893-228X

issn

1520-5010

journal_volume

4

pub_type

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