Carotenoids and polyterpenoids

BRITTON, G.

doi:10.1039/np9890600359

Cited by 13 publications

(3 citation statements)

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“…The pathway is ubiquitous, and over 20 000 naturally occurring isoprenoid metabolites have been identified. End products of the pathway include such important classes of compounds as sterols (Brown & Goldstein, 1979), carotenoids (Britton, 1989), ubiquinones (Bentley et al, 1987), and dolichols (Hemming, 1981). In addition, it was recently discovered that prenylation is an essential posttranslational modification for many proteins that play key roles in membrane structure (Khosravi-Far et al, 1991), signal transduction across membranes (Linder et al, 1991), and transport between organelles (Kinsella & Maltese, 1991).…”

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confidence: 99%

Isopentenyl-diphosphate isomerase: irreversible inhibition by 3-methyl-3,4-epoxybutyl diphosphate

Cd³

1992

Biochemistry

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Isopentenyl-diphosphate:dimethylallyl-diphosphate isomerase (EC 5.3.3.2) catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl diphosphate (IPP) to its allylic isomer, dimethylallyl diphosphate (DMAPP). Incubation of yeast IPP isomerase with 3-methyl-3,4-epoxybutyl diphosphate (EIPP) resulted in a time-dependent first-order loss of activity characteristic of an active-site-directed irreversible process, where k2 = 0.63 +/- 0.10 min-1 and KI = 0.37 +/- 0.11 microM. A 1:1 covalent E-I complex was formed upon incubation with [1-14C]EIPP. The inhibited enzyme was treated with trypsin to give two radioactive fragments, which were purified by reversed-phase HPLC on a C18 column. The modified amino acid in each fragment was identified as C139 by sequencing the radiolabeled peptides. Incubation of IPP isomerase with [2,4,5-13C3]EIPP gave a 13C-labeled E-I complex. A 1H-13C heteronuclear multiquantum correlation spectrum had strong cross-peaks at 1.2/28 and 2.9/48 ppm, which we assigned to the labeled methyl group and C(4) methylene, respectively, of the inhibitor. In addition, a weak signal at 2.17/42 ppm may be from the C(2) methylene. Comparison of these chemical shifts with those of a synthetic adduct isolated from treatment of EIPP with cysteine indicates C139 attacks C(4) of EIPP to generate a thioether linkage between the enzyme and the inhibitor.

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confidence: 99%

Isopentenyl-diphosphate isomerase: irreversible inhibition by 3-methyl-3,4-epoxybutyl diphosphate

Cd³

1992

Biochemistry

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“…Since then reviews have appeared on marine carotenoids by Matsuno and Hirao (ref. 4 ) and on carotenoids and polyterpenoids by Britton (ref,3), both covering literature prior to 1988, and on algal carotenoids (ref. Amongst the around 600 naturally occurring carotenoids which are structurally defined (ref.…”

Section: Introductionmentioning

confidence: 99%

Marine carotenoids: recent progress

Liaaen-Jensen¹

1991

Pure and Applied Chemistry

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“…1 A number of reviews have dealt with natural sesquiterpenoids, 2-7 diterpenoids, [8][9][10][11] sesterterpenoids, 12,13 triterpenoids, [14][15][16][17][18] carotenoids and polyterpenoids. [19][20][21][22][23] Other general reviews are: "Marine natural products". [24][25][26][27][28][29][30] In this review, we show structures of linear furano-and pyrroloterpenoids, and previously reported linear furano-and pyrroloterpenoids where there has been a structural revision or a newly established stereochemistry, previously reported linear furano-and pyrroloterpenoids for which rst syntheses, new bioactivities, or new sources are described are referenced, and this review also added the furanotetraterpenoids and furanocarotenoids.…”

Section: Introductionmentioning

confidence: 99%