Decarboxylation of 1,2,3,4-tetrahydro-beta-carboline-1-carboxylic acids in brain homogenate and catalysis by pyridoxal-5'-phosphate.

Abstract:

:[Carboxyl-14C] labelled 1,2,3,4-tetrahydro-beta-carboline-1-carboxylic acid (I) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline-1-carboxylic acid (II) were synthesized and their decarboxylation was studied in mouse brain homogenate and buffer. The decarboxylation rates of (I) and (II) in the homogenate were about 6-fold and 4-fold, respectively, as compared with the rates in phosphate buffer. The increase could not be prevented by preheating the homogenate, but was partially abolished by addition of 1 mM EDTA. The decarboxylation was increased dose-dependently when pyridoxal-5'-phosphate was included in the buffer, 400 microM being sufficient to exceed the rate in homogenate for both (I) and (II). Mass spectrometric examination of the decarboxylation products indicated that both (I) and (II) were degraded mainly to corresponding 1,2,3,4-tetrahydro-beta-carbolines, but some 3,4-dihydro analogues also were detectable. In conclusion, the results outline a way through which these pharmacologically active beta-carbolines are readily formed under conditions that may be regarded as physiological.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Gynther J,Lapinjoki SP,Airaksinen MM,Peura P

doi

10.1016/0006-2952(86)90173-5

subject

Has Abstract

pub_date

1986-08-15 00:00:00

pages

2671-5

issue

16

eissn

0006-2952

issn

1873-2968

pii

0006-2952(86)90173-5

journal_volume

35

pub_type

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