Zur Kenntnis lokalanästhetisch wirksamer Pyridin‐4‐carbonsäure‐Derivate

Büchi, J; Labhart, P.; Ragaz, L.

doi:10.1002/hlca.19470300208

Cited by 19 publications

(2 citation statements)

References 6 publications

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“…(d) 2-Hydroxyisonicotinate. The methods of Buchi et al (1947) and Baumler et al (1951) were attempted but were not successful. A synthesis modified from that of Boekelheide & Lehn (1961) did, however, yield the required material.…”

Section: Chemicalsmentioning

confidence: 99%

The bacterial oxidation of N-methylisonicotinate, a photolytic product of Paraquat

Orpin

Knight

1972

Biochemical Journal

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Two bacteria have been isolated that are capable of oxidizing N-methylisonicotinate, a photodegradation product of Paraquat (1.1'-dimethyl-4,4'-bipyridylium ion). N-Methylisonicotinate-grown cells of strain 4C1, a Gram-positive rod, oxidized 2-hydroxy-N-methylisonicotinate without lag. Cell-free extracts of these cells converted 2-hydroxyisonicotinate into 2,6-dihydroxyisonicotinate; the reaction did not require molecular oxygen. Maleamate was deamidated and maleate isomerized to fumarate by soluble enzyme systems. [(14)C]Formaldehyde was isolated as the dimedone derivative from the supernatant of a cell suspension oxidizing N-[(14)C]methylisonicotinate, and no [(14)C]-methylamine was detected. Whole cells incubated with N-methyl[carboxy-(14)C]isonicotinate released 95% of the radioactivity as (14)CO(2). The second bacterium, strain 4C2, a Gram-negative rod, did not oxidize any of the mono- or di-hydroxypyridines or their N-methyl derivatives that were available or could be synthesized; nor did cell-free extracts oxidize any of these compounds. Methylamine was oxidized by whole cells without lag; cell-free extracts converted methylamine into formaldehyde when a soluble enzyme system requiring an electron acceptor was used; formaldehyde was oxidized to formate and formate to CO(2) by enzyme systems requiring NAD(+).

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Section: Chemicalsmentioning

confidence: 99%

The bacterial oxidation of N-methylisonicotinate, a photolytic product of Paraquat

Orpin

Knight

1972

Biochemical Journal

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“…by means of kinetic lithiation of this material followed by quenching with carbon dioxide; and since 2,6-dichloroisonicotinic acid can be reduced to 2-chloroisonicotinic acid by a modified Wolff-Kishner reduction, 9 we felt that we should be able to prepare the desired the desired 2,6-dichloroisonicotinic acid, 97% pure by 1 H NMR. Purification appeared to be facilitated by the relatively high solubility of the isomeric 2,6-dichloronicotinic acid present in the crude material.…”

Section: Resultsmentioning

confidence: 99%