Synthesis and absolute configuration of the isomers of homoisocitric acid (1-hydroxy-1,2,4-butanetricarboxylic acid) and the stereochemistry of lysine biosynthesis.

@article{Chilina1969SynthesisAA,
  title={Synthesis and absolute configuration of the isomers of homoisocitric acid (1-hydroxy-1,2,4-butanetricarboxylic acid) and the stereochemistry of lysine biosynthesis.},
  author={K. Chilina and U. Thomas and A. Tucci and K. McMichael and C. M. Stevens},
  journal={Biochemistry},
  year={1969},
  volume={8 7},
  pages={
          2846-55
        }
}
Synthesis and Characterization of the Enantiomerically Pure cis‐ and trans‐2,4‐Dioxa‐3‐fluoro‐3‐phosphadecalins as Inhibitors of Acetylcholinesterase
TLDR
The title compounds are irreversible inhibitors of acetylcholinesterase, and both the kinetic data and the mechanisms of the inhibition are determined by a novel enzyme-kinetic approach that is described in the preceding report. Expand
Synthesis of Enantiomerically Pure 1,5,5‐Trideuterated cis‐ and trans‐2,4‐Dioxa‐3‐phosphadecalins. 31P‐NMR Evidence of Covalent‐Bond Formation and the Stereochemical Implications in the Course of the Inhibition of δ‐Chymotrypsin
The irreversible inhibition of δ-chymotrypsin with the enantiomerically pure, P(3)-axially and P(3)-equatorially X-substituted cis- and trans-configuratedExpand
Generation of glyoxylate in methylotrophic bacteria
TLDR
The results indicate that homoisocitrate cleavage does not occur in any of the methylotrophs tested, and the pathway for oxidation of acetyl-CoA to glyoxylate in Pseudomonas AM1 and organism PAR therefore remains obscure. Expand
Stereochemistry of the Inhibition of δ‐Chymotrypsin with Optically Active cis‐Decaline‐Type Organophosphates: 31P‐NMR studies
Investigation of the inhibition of δ-chymotrypsin with the four novel, optically active, axially and equatorially substitutedExpand
Stereochemistry of the Inhibition of δ-Chymotrypsin with Optically Active Bicyclic Organophosphates: 31P-NMR studies
The inhibition of δ-chymotrypsin with optically active, axially and equatorially substituted trans-3-(2,4-dini-trophenoxy)-2,4-dioxa-3λ5-phospbubicyclo[4.4.0]decan-3-ones ( =Expand
Short and efficient syntheses of (−) -isocitric acid lactone and (−) -homoisocitric acid. Conversion of alkynylsilanes into the corresponding carboxylic acids
Abstract We describe a simple synthesis of natural isocitric and homoisocitric acids from a common intermediate 2. A new method of conversion from a silylated triple bond to the carboxylic acid ofExpand
Wild-type and mutant forms of homoisocitric dehydrogenase in the yeast Saccharomycopsis lipolytica.
TLDR
The results are best explained by the assumption that the active enzyme is a dimer of identical subunits involved in successive dehydrogenation and decarboxylation steps. Expand
Isocitrate lyase from Neurospora crassa: pH dependence of catalysis and interaction with substrates and inhibitors.
TLDR
The pH dependence of the pKi for phosphoenolpyruvate, which binds to the succinate site, suggests that it is dependent on two dissociable groups, one on phosphoenolate and one, by analogy toThe pKm for isocitrate, on the enzyme-glyoxylate-inhibitor complex. Expand
Isocitrate lyase from Pseudomonas indigofera: pH dependence of catalysis and binding of substrates and inhibitors.
TLDR
Inhibition by phosphoenolpyruvate, which binds to the succinate site and may regulate isocitrate lyase from P. indigofera, was twice as pH dependent as that for succinate and the pKi's for maleate and itaconate were similarly pH dependent. Expand
Substrate activity of structural analogs of isocitrate for isocitrate dehydrogenases from bovine heart.
TLDR
D-Garcinia acid, like D-isocitrate, has an alpha-DS-hydroxyl group and a beta-LS configuration of the second carboxyl group, and is a substrate for TPN-linked isocitrates dehydrogenase from bovine heart. Expand
...
1
2
...

References

SHOWING 1-10 OF 20 REFERENCES
Homocitrate formation in Neurospora crassa. Relation to lysine biosynthesis.
TLDR
Neurospora crassa lysine auxotrophs 33933 and STL-7 were found to accumulate homocitrate and malate plus citrate, respectively, and it is shown that, in Neurospora, the initial step ofLysine biosynthesis is via a homocItrate-condensing enzyme which is under effective end product control by lysines. Expand
Accumulation of tricarboxylic acids related to lysine biosynthesis in a yeast mutant.
Abstract Accumulation of tricarboxylic acids related to lysine biosynthesis has been demonstrated in a yeast mutant, Ly12, which requires lysine as a growth factor in synthetic medium but canExpand
Enzymatic formation of cis-homoaconitic acid, an intermediate in lysine biosynthesis in yeast.
TLDR
The enzyme, which has been named cis-homoaconitase, was separated from cis-aconsitase by ammonium sulfate precipitation, has an optimum pH of 8.6 in phosphate buffer, and is inhibited by p-chloromercuribenzoate, α,α'-dipyridyl, and o-phenanthroline. Expand
Homocitric acid accumulation by a lysine-requiring yeast mutant.
TLDR
The excretion of homocitric acid by a lysine-requiring yeast mutant and its conversion into lysin convincingly establish the biosynthesis of lysines in yeast via the previously proposed scheme involving homologues of the citric acid cycle. Expand
Enzymatic formation of alpha-ketoadipic acid from homoisocitric acid.
Biosynthesis of α-ketoadipic acid by extracts of Baker's yeast
A cell-free extract of baker's yeast is capable of converting the carbon atoms of acetate and α-ketoglutarate to α-ketoadipic acid. The co-factors required are coenzyme A, diphosphopyridineExpand
Enzymatic formation of homocitric acid, an intermediate in lysine biosynthesis.
  • M. Strassman, L. Ceci
  • Chemistry, Medicine
  • Biochemical and biophysical research communications
  • 1964
...
1
2
...