Synthesis of 1,2,3,4,4a,10a-hexahydropyrido[3,4-b][1,4]benzodioxins

Coulson, Christopher J.; Wooldridge, K. R. H.

doi:10.1039/j39690002830

Cited by 5 publications

(3 citation statements)

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“…The principal constituents, before the rupture of the benzene ring of tran8-cinnamic acid by a soil pseudomonad, were o-hydroxyphenylpropionic acid and 2,3-dihydroxyphenylpropionic acid (Coulson & Evans, 1959). Blakley & Simpson (1964), in a study of the metabolism of cinnamic acid by a pseudomonad, suggested that the first step is the reduction of the double bond in the side chain, giving rise to phenylpropionic acid, which undergoes hydroxylation in either the orthoor meta-position.…”

Section: Discussionmentioning

confidence: 99%

Degradation of phenylalanine and tyrosine by Sporobolomyces roseus

Moore

Rao

Towers

1968

Biochemical Journal

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Ammonia-lyase activity for l-phenylalanine, m-hydroxyphenylalanine and l-tyrosine was demonstrated in cell-free extracts of Sporobolomyces roseus. Cultures of this organism converted dl-[ring-(14)C]phenylalanine and l-[U-(14)C]tyrosine into the corresponding cinnamic acid. Tracer studies showed that these compounds were further metabolized to [(14)C]protocatechuic acid. Benzoic acid and p-hydroxybenzoic acid were intermediates in this pathway. Washed cells of the organism readily utilized cinnamic acid, p-coumaric acid, caffeic acid, benzoic acid and p-hydroxybenzoic acid. Protocatechuic acid was the terminal aromatic compound formed during the metabolism of these compounds. The cells of S. roseus were able to convert m-coumaric acid into m-hydroxybenzoic acid, but the latter compound, which accumulated in the medium, was not further metabolized. 4-Hydroxycoumarin was identified as the product of o-coumaric acid metabolism by this organism.

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Section: Discussionmentioning

confidence: 99%

Degradation of phenylalanine and tyrosine by Sporobolomyces roseus

Moore

Rao

Towers

1968

Biochemical Journal

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“…An important early observation was that the ternary complex of enzyme, NAD+ and pyruvate slowly gave rise to a new chromophore at about 325 nm with a corresponding decrease in protein fluorescence (Fromm, 1961). It has been proposed that the adduct forms as the result of a reaction between enol-pyruvate and NAD+ at the non-protonated active site of the enzyme (Scheme 1) by a mechanism that is formally analogous to that normally catalysed by the enzyme for the oxidation of lactate (Coulson & Rabin, 1969).…”

mentioning

confidence: 99%

The mechanism of adduct formation between NAD+ and pyruvate bound to pig heart lactate dehydrogenase

Wilton¹

1979

Biochemical Journal

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1. The rate of adduct formation between NAD+ and enol-pyruvate at the active site of lactate dehydrogenase is determined by the rate of enolization of pyruvate in solution. 2. The proportion of enol-pyruvate solutions is less than 0.01%. 3. The overall dissociation constant of adduct formation is less than 5 X 10(-8) M for pig heart lactate dehydrogenase at pH 7.0. 4. The unusual kinetics for adduct formation previously observed in the case of rabbit muscle lactate dehydrogenase [Griffin & Criddle (1970) Biochemistry 9, 1195--1205] may be attributed to the concentration of enol-pyruvate in solution being considerably less than the concentration of enzyme.

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“…Research Department, Pharmaceuticals Division, CIBA-GEIGY Corporation, Summit, New Jersey 07901 Received April 25,1977 A reinvestigation of the reaction of l-benzyl-3,4-dibromopiperidine (2) with the disodium salt of catechol (1) was made, cis-2-Benzyl-l,2,3,4,4a,10a-hexahydro [l,4]benzodioxino [2,3-c]pyridine (5), previously described by Coul-son2 and Berthold,3 was formed along with a slightly greater amount of the undescribed cis-l-benzyll,2,3,3a,10,10a-hexahydro [l,5]benzodioxepino [3,2-b]pyrrole (4). A rationale in accord with previous observations on substitution reactions of 3-substituted piperidines4 is provided for the stereospecific but not regiospecific outcome.…”

Section: Azepinementioning

confidence: 99%