Derivatives of hydroxymethoxy mandelic acid (HMMA), homovanillic

Details Derivatives of hydroxymethoxy mandelic acid (HMMA), homovanillic Derivatives of hydroxymethoxy mandelic acid (HMMA), homovanillic

1991-07-08

1993-11-30

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 55, 560 53, 560 42, 530405, 5303098, 549223, 435793, C07C 6976

Patent

active

052667200

ABSTRACT:
##STR1## Compounds of formula (I), wherein R.sup.1 is hydrogen or hydroxyl. R.sup.2 is a reversibly protected carboxyl group, R.sup.4 is H or C.sub.1 -C.sub.3 alkyl and R.sup.5 is a substituent having a pi electron system alpha to the asterisked carbon atom, and containing one or more of a carboxyl, an amine, or an aldehyde group, are prepared by reversibly protecting the carboxyl group of hydroxymethoxy mandelic acid or homovanillic acid and reacting the phenolic hydrogen with an alkylating agent such as methylbromoacetate, to introduce an ester group, followed by selective hydrolysis. The compound of formula (I) can be coupled, for example by means of an active ester, to either a carrier protein for the preparation of an immunogen, or to a label, such as a fluorescent label, a radioisotope, or an enzyme.

REFERENCES:
patent: 4041076 (1977-08-01), Avenia et al.
J. Immunological Methods vol. 118, No. 1 (Mar. 1989) Mellor et al "Production and characterization of antibodies . . . " pp. 101-107.
J. Clin Chem. Clin. Biochem., vol. 22, No. 11, (1984) Knoll et al "Problems in the development of radioimmunoassay . . . " pp. 741-749.
Int. J. Peptide Protein Res.s, vol. 30, No. 2, (1987) Albericio et al "An acid-labile anchoring linkage for solid-phase synthesis . . . " pp. 206-216.
Chemical Abstracts, vol. 76, No. 15, (Apr. 1972) Liebman et al "Synthesis of homovanillic acid-2-. . . " p. 394, Abstract 85528v.

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